Chicago Travelers Recommend

Whether spending a weekend in the Windy City or planning a midweek adventure, you have plenty of time to discover Chicago’s highlights in two days. From world-class museums and world-ranking skyscrapers to the city’s delectable dining scene, here’s how to make the most of your 2-day stay.

Day 1: The Loop and Beyond

Morning: Set right along the waterfront, Chicago’s Museum Campus (home to the Field Museum of Natural History, the Adler Planetarium, the Shedd Aquarium, and more) is the perfect place to immerse yourself in the Windy City’s cultural side.

Afternoon: The Loop, Chicago’s downtown business district, is home to a heavy concentration of landmarks. The neighborhood is ideal terrain for walking tours—explore on foot and stumble across highlights ranging from Millennium Park and the Willis Tower (formerly the Sears Tower) to public sculptures by Pablo Picasso and Alexander Calder.

Night: Head up to the top of the Willis Tower, where you can enjoy a multicourse meal while taking in views of Chicago lit up after dark. Alternatively, a dinner cruise along Lake Michigan combines gourmet dishes with splendid skyline views.

Day 2: Sand and Surf, Snacks and Sightseeing

Morning: On Chicago’s 26-mile (42-kilometer) shoreline, admire what might look to be the ocean—a stretch of Lake Michigan often called the “Third Coast.” When the sun’s out, follow Chicagoans to the lake’s sandy beaches, from North Avenue Beach to Oak Street Beach. Alternatively, enjoy waterside attractions of a different kind at Navy Pier.

Afternoon: Complete this day with a food tour of Chicago’s vibrant culinary culture. Seek out hot dogs and Italian beef sandwiches, and save extra room for deep-dish pizza. A number of renowned, decades-old pizza joints can be found right in the Loop, from Lou Malnati’s and Giordano’s to Gino’s East.

Night: When the sun is setting, embark on a helicopter tour and get rewarded with a unique, aerial perspective of the city. Spot Chicago’s most distinctive skyscrapers, discover its different neighborhoods from the air, and see the lights come on as evening descends.

Chicago makes up for its blustery winters with summer sunshine and high temperatures. Whether you choose to spend a day in the city’s parks, lounge on one of Lake Michigan’s beaches, or retreat to the air-conditioned calm of a museum when the afternoon sun feels particularly strong, here’s how to spend summer in the Windy City.

• Go for a cruise along the Chicago River, and admire the city’s famous skyscrapers from the water’s edge.
• Couple a sightseeing excursion to Millennium Park with a night of music at the Chicago Jazz Festival.
• Enjoy unparalleled fireworks views when you celebrate the Fourth of July aboard an all-night party yacht.
• Head to Grant Park, and come hungry: The Taste of Chicago Festival is one of the city’s most popular summer events.
• Retreat to the Art Institute of Chicago for a cultural immersion when the thermostat soars (or when summer thunderstorms roll in).
• Enjoy a celestial show at the Adler Planetarium —and go stargazing at its companion Doane Observatory.
• Sun yourself on one of Lake Michigan’s sandy beaches, such as North Avenue Beach or Oak Street Beach.
• Combine a fresh-air stroll with the opportunity to chow down during a food-themed, neighborhood walking tour.
• Commune with aquatic life during an excursion to the delightful Shedd Aquarium.
• Indulge in an urban oasis when you visit the blossoms at the Chicago Botanic Garden.

Chicago may be 1,000 miles from the ocean, but the city is still best seen aboard a boat. From the Chicago River to nearby Lake Michigan, visitors are spoiled for choice when it comes to touring the city from the water. See below for your options.

Chicago River Cruises

Learn the history of Chicago’s skyscrapers on a Chicago River cruise, some of which focus specifically on the city’s towering architecture. See Sears Tower and the Wrigley Building while enjoying a casual architecture cruise, and hear how the flow of the river was reversed—a feat of modern engineering.

Sailing and Speedboat Rides on Lake Michigan

Lake Michigan is so big that its total area is larger than that of nine different US states, meaning you’ll feel like you’re cruising the open ocean on a sightseeing lake tour. Take a speedboat tour, dine on an evening buffet cruise, or enjoy a private sunset sail to see where the Chicago skyline rises up from the water and faces the deep blue horizon.

Combo Tours

If you can’t decide between the river and lake, choose a Chicago combo tour that includes both experiences. You’ll enjoy a casual cruise of the river and then race down Chicago’s coastline on a speedboat ride.

Chicago is blessed with world-class museums, extraordinary skyscrapers, beautiful beaches, and fabulous restaurants—and happily, it’s easy to take advantage of its highlights with the kids in tow. From river cruises and Segway adventures to pizza-themed food tours, here’s how to plan a family-friendly day out in the Windy City.

• Get a bird’s-eye perspective on the Windy City when you ascend to one of its skyscraper observation platforms: the Willis Tower’s Skydeck and 360 Chicago Observation Deck both offer unbelievable views.
• Exploring by boat is the perfect way to make sightseeing exciting for younger visitors. Wend your way along the Chicago River, or even head out on Lake Michigan.
• Chicago is a dream city for museum lovers—and cultural highlights like the Field Museum of Natural History, Adler Planetarium, and Art Institute of Chicago are fun to explore with the whole family.
• If you’ve got older kids in tow, enjoy a speedy way of discovering Chicago’s major landmarks when you zip around town by Segway or by bike.
• Given that Chicago’s culinary specialties include pizza and hot dogs, a wide-ranging tasting tour is sure to please kids and adults alike.

Chicago is famous for its architecture, especially its towering skyscrapers, and you can see it all on an architecture tour. Because building design evolved as the city grew, there’s plenty to learn about the storied history—here’s where to start.

Willis Tower — once the tallest building in the world

Formerly known as the Sears Tower, this downtown skyscraper stands 108 stories high, making it the second tallest building in the US. The 103rd-floor Skydeck offers spectacular views, and a step out onto the Ledge lets you look straight down to the street below. Make it a stop on a hop-on hop-off bus tour or book VIP access for breakfast, lunch, or dinner at the Skydeck. It’s also visible from most river and downtown walking tours.

John Hancock Center — offering the best views of Lake Michigan

The fourth-tallest building in the city, the John Hancock Center features a 94th-floor observatory and a 95th-floor restaurant, as well as the best views of Lake Michigan in the city. Don’t miss TILT—an enclosed glass platform that tilts guests out over Michigan Avenue from the 94th floor. Stop off at the center during a bus tour or see it from above on a helicopter tour of the city. 

Marina City — Chicago’s “corn cob towers”

Shaped like two corn cobs standing tall along the Chicago River, the Marina City towers were once the tallest residential buildings in the world. Today, they’re home to a mix of commercial and residential uses, including a hotel, bowling alley, several restaurants, and the House of Blues concert hall. View Marina City from an architecture boat cruise or a kayaking tour on the Chicago River.

Tribune Tower — neo-Gothic design on Michigan Avenue

Overlooking the Chicago River, the Tribune Tower features dozens of stones and bricks from historically significant sites all over the world, including fragments from the Berlin Wall, the Parthenon, the Great Wall of China, and Angkor Wat. View the tower on an architecture boat cruise or a walking tour of historic skyscrapers.

Wrigley Building — lighting up the Magnificent Mile

Across the street from Tribune Tower, the Wrigley Building was the first major office building north of the Chicago River. Check it out from the river below or by joining a walking tour of historic skyscrapers.

Chicago Cultural Center — stunning stained-glass domes

The Italian Renaissance-inspired interior of the Chicago Cultural Center (which formerly hosted the city’s central library) features gorgeous stained-glass domes, colorful mosaic floors, and walls made of green, white, and pink marble. Take a walking tour of the Loop focused on interior architecture or Tiffany glass.

From skyscrapers to museums to vibrant neighborhoods to public parks, Chicago has something for everyone, and three days is more than enough time to explore its highlights. Travel by bus, bike, or on foot; linger in the bustling Loop; or head out of town on a day trip. Here’s how to plan your 3-day Windy City itinerary.

Day 1: Chicago’s Top Attractions

Explore Chicago’s most popular landmarks, many of which are concentrated in the Loop neighborhood, including Millenium Park and the Willis Tower Skydeck. Bus and bicycle tours of the area make it possible to see more in less time, while a hop-on hop-off bus itinerary offers a seamless overview of the city (plus the chance to disembark where and when you wish). Alternatively, combine your Loop adventures with a trip to another part of town. Catch an afternoon Cubs game at Wrigley Field on the North Side, or head to the South Side to explore Chinatown.

Day 2: Museums, Architecture, and Other Historical Highlights

Learn about Chicago’s past on an architecture tour—hop aboard a riverboat and cruise all three branches of the Chicago River, spotting highlights such as the Tribute Tower and the Merchandise Mart as you go, or head off on an intimate walking tour to view landmarks firsthand. Then, delve into Chicago’s esteemed museums, including the Field Museum of Natural History, Museum of Science and Industry, and the Art Institute of Chicago.

Day 3: Chicago Area Day Trip

Frank Lloyd Wright, a longtime Chicago resident and one of the 20th century’s most celebrated architects, designed a number of buildings in the Chicago area. Discover some of his best-known works on a day trip to the Frank Lloyd Wright Home and Studio in Oak Park, a village located just beyond Chicago’s western edge. Here you'll discover where the architect lived and worked for the first two decades of his career, and where he developed his signature Prairie School style. Oak Park’s other architectural gems include the Frank Lloyd Wright Historic District, Unity Temple, and the Arthur B. Heurtley House.

Poet Carl Sandburg famously described Chicago as “the City of the Big Shoulders,” and it’s true that this city has extraordinary breadth. Home to record-breaking skyscrapers and enviable lakefront views, world-class museums and dynamite restaurants, a buzzing downtown and historical neighborhoods packed with charm, Chicago is an utterly unique study in contrasts. Whether you wish to admire its architecture from the water’s edge, ascend to the top of one of the Western Hemisphere’s highest buildings, learn about the city’s sordid Prohibition dealings, or admire priceless canvases, this Midwestern powerhouse serves up a dazzling range of entertainment and sightseeing possibilities, no matter your interests. To help you narrow down the options, browse this collection of must-do activities—and get ready to make the most of your Windy City excursion.

You don't need a car to get around Chicago, thanks to a world-class public transit system, compact neighborhoods, and an easy-to-navigate grid layout in the downtown Loop area. Whether you’re keen to explore on foot, by train, or even via the city’s waterways, here are your options for making your way around the Windy City. 

Ride the “L” Train

Chicago claims the second-largest public transit network in the US, made up of buses and the city’s signature elevated rail lines, plus underground and street-level trains. You can buy single-ride tickets directly from bus drivers or via vending machines at rail stations. If you're planning to ride frequently, save with a 1- or 3-day unlimited pass. 

Hop On and Hop Off

If taking public transit seems daunting but you still want the flexibility to explore at your own pace, a hop-on-hop-off-bus tour is a user-friendly option. Multiple routes and dozens of stops can get you almost anywhere you want to go in Chicago, and you can learn about passing sights along the way through narration.

Catch a Water Taxi or Cruise

With many attractions along the Lake Michigan shoreline and the snaking Chicago River, Chicago can also be explored by water. Catch an affordable water taxi for a fun way to get between landmarks such as the Magnificent Mile, Chicago Riverwalk, and Chinatown. Architecture cruises are a popular way to learn about the city’s signature structures, while Lake Michigan cruises offer a new vantage point on the Chicago skyline, often with included dinner and drinks. 

Take a Walk

Chicago is defined by its neighborhoods, so soak up local character on a stroll through walkable “villages” such as Wrigleyville, Hyde Park, Andersonville, Wicker Park, and River North. Walking tours can help you discover ethnic eateries, architectural gems, gangster history, and more. 

Bike or Roll on a Segway

To cover more ground and fit in multiple neighborhoods, rent a bike or Segway and explore the city on two wheels. Guided tours can show you the best sightseeing routes, from the Lake Michigan shoreline to Loop landmarks or small-batch breweries.

Chicago’s skyline ranks among the most impressive on the planet, thanks to its magnificent skyscrapers representing numerous architectural styles. One of the best ways to experience the sights and sounds of the “Windy City” is while floating down the Chicago River. Here’s what you need to know to make a voyage yourself.

Highlights

• Take an architecture river cruise to learn why Chicago’s skyline is so impressive.

• Float past more than 40 notable buildings, including the John Hancock Building, Aon Center, Wrigley Building, and Willis Tower.

• See the illuminated waterfront, including the Buckingham Fountain, on a night cruise of the Chicago River and Lake Michigan.

• Combine a river cruise with a trolley city tour, minibus sightseeing tour, helicopter ride, or early access to the Willis Tower Skydeck.

• Chicago sightseeing cruises are offered aboard speedboats and double-decker riverboats.

Fall is a wonderful time to visit Chicago. Crisp breezes and golden leaves lend the Windy City a romantic, autumnal ambiance, but it’s still warm enough to enjoy open-air bus tours, cruises along Lake Michigan and the Chicago River, and engaging walking tours. Here’s what to do during your fall visit to the Windy City.

• Explore the city by boat, and catch glimpses of its most striking buildings, on an architecture river cruise.

• Admire stunning city views from the lofty heights of the 360 Chicago Observation Deck.

• Discover a true Chicago icon when you visit the world-famous Willis Tower.

• Visit Al Capone’s former haunts (and learn about the city’s sordid past) on an alternative history tour.

• See where the Cubs made World Series history on a walking tour of Wrigleyville.

• Sip acclaimed Illinois wines aboard a Lake Michigan boat tour.

• Use a Chicago Explorer Pass to craft your own sightseeing itinerary (and visit the city’s top museums and attractions).

• Make the most of your time in the Windy City on a h op-on hop-off bus tour.

• Get to know Chicago’s spooky side during a Halloween-themed bike tour.

• Step back in time to the Roaring Twenties at a speakeasy-themed dinner show.

If you only have one day to see Chicago, don’t worry. That’s more than enough time to get acquainted with the Windy City’s ineffable style, lofty skyline, and numerous cultural attractions. From architecture cruises along the Chicago River to skyscraper observation decks, here are some suggestions for the perfect sightseeing day in Chicago.

Morning: Chicago’s Green Spaces

Start your day by looking beyond Chicago’s urban jungle of skyscrapers. The city has plenty of vibrant green spaces to be seen by bike or Segway tour. Millennium Park, within the larger Grant Park, has become one of the city’s most popular attractions since it opened in 2004. Stretching across 25 acres (10 hectares), the park’s highlights range from the verdant Lurie Garden to the playful Crown Fountain and Anish Kapoor’s reflective Cloud Gate sculpture, commonly known as “The Bean.”

Afternoon: Architectural Sights

From the soaring spires of the Willis Tower and the John Hancock Center to the famous Marina City buildings and the landmarks along Magnificent Mile, Chicago is an architecture lover’s city. One of the best ways to take in the sights is on a cruise along the Chicago River. Find a seat on the deck, and crane your neck upward as your tour guide shares stories about how the city’s skyline came to be. Alternatively, a walking tour lets you get intimate with the landmarks, head into building lobbies to admire interior architecture, and delve into their history.

Evening: Aerial Views

Chicago is a skyscraper city—until One World Trade Center debuted in New York City in 2013, the Willis Tower (formerly known as Sears Tower) was the tallest building in the Western Hemisphere. In addition to being a Chicago landmark, the building offers some of the best views of the cityscape and Lake Michigan beyond. Book Skydeck admission tickets to take an elevator 100 floors above the city and admire a panoramic perspective of Chicago after dark. If that isn’t sufficiently lofty, evening helicopter tours also provide an excellent aerial vantage point for night sightseeing.

The Prohibition Era was a colorful time in the "The Windy City" with mobs and gangs running rampant—everyone from Al Capone to John Dillinger—and plenty of speakeasies where the liquor flowed. Here are the options to learn more about the era on a gangster tour of the city.

Mafia and Prohibition History in Chicago

See the spots once ruled by liquor, jazz, and the mafia on a Prohibition history tour. Visit relevant sites such as the Holy Name Cathedral, Biograph Theatre, Clark Street Bridge, and the site of the St. Valentine’s Day Massacre in 1929. Private tours include a Chicago nightlife option and a Chicago blues and Jazz Age history option.

Speakeasy & Cocktail Tours

Another way to experience the city’s Prohibition era is to visit the pubs and bars that defied the 10-year alcohol ban. Speakeasy bars across the Old Town district, Wicker Park, and the Chicago Loop come to life on cocktail-themed tours.

Crime and Gangsters Tours

Learn about the Chicago crime of the past and take a trip back in time to the 1920s, ‘30s, and ‘40s on a crime and gangster tour. Hear stories about the iconic murders and crime scenes from this infamous time in the city's history. Explore Chicago's North Side, Lincoln Park, Gold Coast, Magnificent Mile, and other neighborhoods that are part of the city's gangster past.

Spring in Chicago brings a gentle thawing of the winter snows, newly balmy temperatures, and more excuses than ever to go exploring. From bike tours to hop-on hop-off bus journeys, Lake Michigan cruises to foodie-frequented walking tours, here’s what to do during your springtime visit to the Windy City.

• Admire Chicago’s ineffable skyline from the water’s edge during a Lake Michigan sightseeing cruise.

• Take in stunning city views with a glass of prosecco in hand atop the 360 Chicago Observation Deck.

• Zip through Chicago’s neighborhoods and enjoy the fresh spring breeze on a Windy City bike tour.

• Pair local nibbles with a springtime stroll during a culinary walking tour of the Loop.

• Dine and dance with abandon while taking a sunset cruise.

• Score a seat on the top deck during a hop-on hop-off Chicago bus tour.

• Plan your own cultural itinerary and explore Chicago’s many museums.

• Fuel up with an indulgent visit to a Chicago-style pizzeria(or several).

• See the neon-lit cityscape during a nighttime helicopter tour.

• Trade the urban bustle for a day in southwest Michigan’s burgeoning wine region.

Chicago’s friendly neighborhood feel and proud industrial roots make it a welcoming city for travelers on a budget. With abundant museums, casual eateries, and public parks connected by an efficient public transit system, it's easy to experience the best of Chicago cuisine and culture without breaking the bank. Here's how.

Explore More with a Sightseeing Pass

Save big on Chicago's top attractions with a sightseeing pass such as the Go Chicago Explorer Pass or Chicago CityPass. Customize a pass with your choice of attractions such as the Shedd Aquarium, Skydeck Chicago, Museum of Science and Industry, and Adler Planetarium, and enjoy discounts of up to 40 percent on admission. 

Get Around on a Hop-On-Hop-Off-Bus Tour

Avoid the expense of car rental by utilizing Chicago's excellent public transit network or booking a hop-on-hop-off-bus tour. These affordable and user-friendly tours combine narrated sightseeing with the flexibility to design your own itinerary, with stops at dozens of Chicago's must-see landmarks. Bonus: The buses are heated during Chicago’s famously frigid winters.

Visit Top Chicago Museums

Chicago's world-class museums are a great way to get cultured on the cheap. From creative collections at the Art Institute of Chicago to science-focused exhibits at the Field Museum and Adler Planetarium, there's something for everyone. Check local event listings for museum free days to save even more. 

Find Budget-Friendly Bites

Happily for budget travelers, most of Chicago's signature dishes are heavy on taste but light on the wallet. Look for abundant street fare and casual eats such as deep-dish pizza, loaded Chicago hotdogs, and popcorn. Chicago food tours can show you how to find the most authentic snacks and bars in the city, often for less than the price of a single fine-dining meal.

Food is a big deal in Chicago, but if there’s one dish most associated with the “Windy City,” it’s Chicago-style pizza. This gooey, cheesy, deep-dish pizza, characterized by its thick cornmeal crust, was invented by Pizzeria Uno in 1943. Here’s how to try it.

Dining Experiences

Cross two items off your Chicago to-do list with a sky-high meal at Skydeck, the observation deck at the top of the Willis Tower. Tuck into a Chicago-style pizza while taking in the evening views of the city below. While deep-dish pizza is the city’s most popular style, the pizza scene is more diverse than that. Explore the food culture on a pizza-centric bus tour, with stops to sample slices ranging from deep-dish to thin crust.

Neighborhood Food Walking Tours

Each Chicago neighborhood has its own distinct personality (and usually a few pizza joints). One of the best ways to experience the food scene is to hit the pavement on a culinary walking tour in neighborhoods such as Old Town, Gold Coast, River North, Wicker Park, Bucktown, Naperville, Lincoln Square, or West Loop. Dive deep into the city’s Italian heritage with samples of pizza and Italian beef on an Italian food tour, or take your stomach on a walking tour of Chicago’s other famous foods, such as Chicago dogs, Italian beef sandwiches, popcorn, and chocolate.

Don't let the rain stop you from making the most of your time in Chicago—many of the Windy City's must-see sights are actually indoors, so there's no need to hole up in your hotel room. Here are a few ideas for rainy days in Chicago.

• See the gray skies from a new point of view on the glass-enclosed balcony at the Willis Tower's 103rd-floor Skydeck.
• Bring the kids (or your inner child) to the LEGOLAND Discovery Center.
• Stay out of the rain at one of the city's myriad museums, such as the Field Museum of Natural History, the John G Shedd Aquarium, or the Chicago Children's Museum.
• The famous Chicago Pedway, a network of underground tunnels and overhead bridges, runs throughout the downtown area, making it easy for both locals and visitors to avoid the elements and get around without ever stepping foot outside.
• See the city's sights and architecture at street level without getting wet on a hop on, hop off bus tour or a guided sightseeing experience by bus.
• Come nightfall, catch some live music at the House of Blues or a show at the Briar Street Theater to stay dry.

The Windy City may be famous for its snowfall, but don’t let that dissuade you from visiting. Chicago transforms into a winter wonderland during the cold months. Explore its holiday light displays, visit its festive markets, and enjoy cozy stints in the city’s museums and speakeasies. Here’s how to plan the perfect winter getaway to Chicago.

• Pair a visit to the sky-high Willis Tower Skydeck with a Chicago-style pizza meal.

• Visit some of the Windy City’s coziest and most atmospheric speakeasies during a Prohibition-themed tour.

• When the weather is frightful, enjoy an indoor day at the Field Museum of Natural History, Art Institute of Chicago, or Adler Planetarium.

• Visit Christmas markets, skating rinks, and other seasonal attractions during a holiday stroll and food tour.

• View the Windy City from the sky during a ride in a helicopter that’s been decorated with holiday lights.

• Discover the city’s holiday light displays by trolley, private vehicle, or Segway.

• Plan a New Year’s Eve to remember by booking a luxury dinner cruise on Lake Michigan.

The Windy City is a destination of icons—famous foods, sports teams, architectural wonders, and historic blues bars. It’s a multifaceted metropolis with a lot going on, both on and off the tourist path. Here are a few ways to experience Chicago like a local.

Highlights

• Hit the waters of Lake Michigan during a private sailing excursion along Chicago’s stunning lakefront.

• Explore Chicago’s top-notch craft beer scene with a ride on the Brewery Barrel Bus.

• Grab a paddle and go kayaking at twilight to watch the fireworks over Navy Pier.

• Skip the line at one of Chicago’s top museums, including the Art Institute of Chicago, Alder Planetarium, Museum of Science and Industry, or Field Museum.

• Indulge in a favorite Chicago pastime—retail therapy—with a shop and spa tour along the Magnificent Mile.

• Rent a bike and hit the pavement for a self-guided tour of Chicago’s vibrant and diverse neighborhoods.

Home to everything from bars and craft breweries to comedy clubs and critically-acclaimed restaurants, the Windy City has a lot to offer after the sun sets. Here are a few of the best ways to spend an evening in Chicago. 

Prohibition-Themed Excursions

Chicago’s insalubrious past has since become part of the Windy City’s allure; 1920s and ’30s-themed tours typically introduce you to former residents such as Al Capone and visit some historic speakeasies. Book an evening excursion to discover local history and enjoy classic cocktails in flapper fashion.

Craft Beer Crawls

The existence of dozens of breweries show that Chicago takes its beer seriously. Explore some of the city’s pioneering breweries and destination-worthy bars on a bar crawl or freewheeling beer tour, and leave the logistics (and driving) to your guide.

See a Show

The Windy City is packed with theaters and performance venues, all of which offer after-dark entertainment. If you’re visiting with kids, take in a blockbuster musical at the Loop’s historical theaters. Or, if you’re into late-night laughs, Chicago has a surfeit of comedy clubs, including the renowned Second City.

Dinner Cruises

Combine sightseeing with dinner on an evening cruise of the Windy City’s waterways. Whether you sail on the Chicago River or head to the waters of Lake Michigan for glittering skyline views, you’ll enjoy gourmet eats, delectable wine pairings, and incomparable scenery. 

Chicago is a city with style and verve, and its beautiful parks, picturesque waterways, and vertiginous heights all make the perfect backdrop to a romantic excursion. From 2-passenger helicopter flights to Lake Michigan cruises and after-dark speakeasy visits, here’s how to enjoy a special trip to Chicago with your significant other.

Cruise Lake Michigan at Sunset

Lake Michigan is almost oceanic in scope, and a night out on the water is a classic Chicago experience. Book an early evening tour to watch the sun descend over the iconic Chicago skyline, and enjoy a romantic moment out on the deck. Alternatively, a dinner cruise—complete with gourmet dishes and flutes of sparkling wine—is the perfect way to toast a special occasion.

Enjoy a Couple’s Photo Shoot in Millennium Park

Visit one of the Windy City’s most in-demand sightseeing destinations—and enjoy a special way to record your memories for posterity—when you book a couple’s photo shoot. Explore the greenery and public artworks of Millennium Park, admire the perspective on the Loop’s gleaming skyscrapers, and see the famous Cloud Gate sculpture by Anish Kapoor—better known as “The Bean.” Your very own photographer will be present to show you the sights and capture your romantic moments.

Sip Cocktails in the City’s Speakeasies

During its Prohibition-era heyday, Chicago was filled with speakeasies (not to mention infamous gangsters the likes of Al Capone). Today, that legacy lives on in the city’s plethora of top-notch cocktail haunts (which, today, are thankfully free of bathtub gin). Book a speakeasy tour for a dose of history and to discover a number of cozy, candlelit drinking dens with your significant other.

Book a Private Helicopter Tour

Few views of Chicago can compare with the ones afforded by a helicopter—and taking to the air on a freewheeling journey above the skyscrapers is one of the city’s most popular romantic experiences. Book a private flight for a particularly intimate experience, and enjoy an indulgent accompaniment in the form of Champagne and chocolates.

Chicago is a food-lover's dream, as there’s no shortage of great dining experiences to satisfy any palate. From Chicago-style hot dogs and deep-dish pizza to diverse cuisine from around the world, here are a few ways to make the most of your visit.

Pizza Tours

It should come as no surprise that you’ll have plenty of options to choose from when it comes to pizza in Chicago. Walking and bus tours highlight the city’s unique take on deep-dish, coal-fired, and other styles, and you can even take a cooking class to learn how to make Chicago’s most popular dish yourself. 

Dining at the Skydeck

Enjoy VIP after-hours access to the Skydeck at the Willis Tower, one of the tallest buildings in the Western Hemisphere. Dine on a three-course meal featuring Chicago-style deep-dish pizza with your choice of toppings while taking in incredible views of the city from the 103rd floor. Breakfast and lunch options are also available, with each experience lasting about two hours.

Dinner Cruises

Cruise Lake Michigan on a luxury yacht while enjoying a gourmet three-course meal and amazing views of the Chicago skyline. Departing from Navy Pier, cruises last about three hours. On summer Wednesdays and Saturdays, upgrades are available to include the fireworks show over Navy Pier.

Neighborhood Food Walking Tours

There’s no better way to get to know the unique ethnic flavors of Chicago’s neighborhoods than a food walking tour. Sample Vietnamese cuisine in Argyle, Scandinavian in Andersonville, or Polish in West Town. Learn about Chicago history over pizza in the Gold Coast, German fare downtown, or a Chicago-style hot dog in Wrigleyville.

The Windy City offers plenty of cultural, recreational, and culinary attractions, but destinations beyond the city limits let you explore the best of the region too. From national parks and destination-worthy wine regions to nearby cities, here are some of the most enticing day trips from Chicago.

Naperville – about 28 miles (45 kilometers) away

Head just outside Chicago city limits and venture to charming Naperville. The Chicago suburb, home to roughly 150,000 people, is a city in its own right. Trains link the two destinations, and full-day tours make getting there simple. Upon arrival, browse the shops and restaurants in Naperville’s downtown and stroll along the Riverwalk. For an unconventional way to explore the area, try a smartphone scavenger hunt game featuring Naperville’s key attractions.

Indiana Dunes National Park – about 49 miles (79 kilometers) away

Though Indiana Dunes National Park is only a quick drive around Lake Michigan’s southernmost shore from Chicago, the park feels a world away with its beachy ambiance and Saharan sand dunes. Enjoy a day at the beach; explore the titular dunes, marshes, and forests; and even discover (and taste) the highlights of the Duneland Wine Country on a full-day tour.

Milwaukee – about 83 miles (134 kilometers) away

Book a day trip to Milwaukee, Wisconsin, and head across state lines to discover another thriving city. As the historic home of the Miller Brewing Company, Pabst Brewing Company, and a slew of modern craft breweries, Milwaukee is renowned for its long-running beer scene. The cosmopolitan city also boasts the impressive Milwaukee Art Museum, soaring Milwaukee City Hall, and other attractions. A one-day tour is enough time to discover the highlights.

Southwest Michigan – about 90 miles (145 kilometers) away

Discover the thriving Great Lakes wine region, and sip in style on a full-day excursion from Chicago to scenic southwest Michigan. The Lake Michigan Wine Trail features dozens of banner wineries. Rieslings, pinot gris, and Rhone varietals are some of what’s planted on Michigan’s slopes, and you can find a selection of fruit wines and brandies, too. Head out on a full-day tour—and leave the driving to your guide.

Indianapolis – about 185 miles (298 kilometers) away

Indiana’s thriving state capital, Indianapolis offers one more incentive to travel across state lines. The accessible city is a popular choice for visitors of all ages as it's home to the famous Speedway, which hosts the Indianapolis 500, as well as museums and other cultural stops. Take part in a scavenger hunt game for a fun-filled sightseeing option, go on a guided walk of the Indy Beer Mile, or follow a local guide to the tasty eateries of Massachusetts Avenue.

Chicago has long been a cultural melting pot, one where different culinary influences all bring something of their own to the table. With such a strong food scene, it can be hard to know where in the Windy City to start. From deep-dish pizza to Chicago dogs, here are our picks for can’t-miss food experiences.

Must-Try Dishes

It’s easy to detect the strong Italian influence on Chicago’s culinary scene; after all, some of the city’s most iconic dishes reflect this tradition. Don’t miss deep-dish pizza, known for its buttery crust, bright tomato sauce, and generous sprinkling of mozzarella. Sandwich lovers should sample an Italian beef : a roll topped with thinly sliced roast beef and sweet or hot peppers, then dipped in its own cooking liquids. And Chicago’s sizable Mexican community has made tacos a must-eat as well.

With two pro baseball teams in town, the prevalence of Vienna hot dogs should come as no surprise, but unlike in New York City, Chicagoans load up their hot dogs with mustard, peppers, pickles, relish, tomatoes, and celery salt—but no ketchup. If you head to a stadium, sample Chicago mix popcorn, made with a combination of caramel- and cheese-coated kernels.

Must-Do Experiences

• Eat your way through the Chicago food scene—pizza, Chicago-style hot dogs, local chocolate, and craft beer—on a guided walking tour of some of the city’s best restaurants.

• Treat yourself to an unforgettable meal on the Willis Tower Skydeck, which rises 1,353 feet (412 meters) above Chicago.

• Enjoy a sunset dinner cruise aboard a luxury yacht on Lake Michigan—the city’s iconic skyline makes for a wonderful backdrop.

• Cycle your way through neighborhoods like Wrigleyville, Old Town, Lakeview, and Lincoln Park while stopping to fuel up at local culinary haunts.