Chicago Trip Planning & Itineraries

Day One: Chicago Tours

Chicago's main attractions are conveniently clustered around the city center. Save your hard-earned dollars with the Chicago CityPass, giving you discounted admission to five of the city's premier attractions: Hancock Observatory, Field Museum, Museum of Science & Industry, Adler Planetarium and Shedd Aquarium. Next, we'll help you embrace Obamamania on your visit to Chicago, with our rundown of essential Windy City experiences. And to get around, take your pick of cruises by water, coach tours by land and exhilarating Segway tours. Or tour Chicago your own way on a Hop-on Hop-off Trolley Tour, with stops at the city's most popular attractions. To get that all-important overview of Chicago, get things rolling with a comprehensive Grand Half-Day Tour of the city. Covering the North Side and South Shore, and a drive along the length of the scenic Outer Drive, you'll also tour Lincoln Park, Washington Park and Grant Park. Or combine the tour with panoramic views of Chicago from atop the 94th floor of the Hancock Tower. Now you've got your bearings!

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Day Two: Chicago Architecture Tours

Chicago is famous for its Art Deco and skyscraper architecture, so taking a tour of the Windy City's architectural highs and lows is a great way to get to know this town. Icons from the famous Chicago School of Architecture are revealed on the Historic Loop Skyscrapers walking tour of Chicago's earliest skyscrapers, built between the 1870s and the 1930s. For contrast, follow up with the Modern Loop Skyscrapers walking tour of Chicago's modern and post-modern architectural gems. Classic Art Deco detailing from the 1920s and '30s is the theme on the Downtown Chicago Deco walking tour, and Tiffany on Wednesdays highlights the dazzling stained-glass creations of Louis Comfort Tiffany. The South Shore Tour packs in a visit to the Art Institute of Chicago and its renowned collections spanning 5,000 years of artistic expression in Europe, Asia, Africa and the Americas.

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Day Three: Chicago Great Outdoor Tours

Get on your bike to tour Chicago up close like a local. Start with the Lakefront cycling tour of quiet back streets, city parks, and North Side beaches. Explore more of Chicago's neighborhoods by bike, cycling through the Gold Coast, Old Town, Lincoln Park and Lakeview. Or just hire a bike for the day and plan your own Chicago cycling tour. And as the sun sets, take a memorable city lights bike ride to see Chicago at her finest. Now you've seen Chicago by land, see the sights by water on a river cruise, highlighting the city's river and lakeside architectural triumphs. Take an adrenaline-charged ride in a speedboat across Lake Michigan, or relax into the evening on a romantic dinner cruise. Then take the action indoors on a Chicago Club Crawl, visiting two of the city's local blues clubs for an unforgettable night on the town.

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Twin Anchors

Twin Anchors' famous baby back ribs are something of a city identity, so don't leave Chicago without sampling 'em. Choose fries, onion rings and baked potatoes for sides, and soak up the 1950s supper-club ambience oozing from the Sinatra-centric jukebox.

Signature Room

The sky's the limit at Signature, perched up high on the 95th floor of the John Hancock Center. That stunning view is free, and menus run from buffet lunches to dinner, epicure and pre-theater options featuring seafood and Chicago steaks.

Topolobampo

Leave the adjoining Frontera Grill for lunch, and head to Topolobampo for finely tuned high-end Mexican fare. Creativity is the buzz word here, with menus changing nightly. Reservations a must.

Cass Hotel

It's hard to imagine that this property was bare-bones basic not too long ago. In late 2007 the remodeled Cass emerged as a chi-chi boutique hotel, with hip colors and high-tech toys to ensure your stay is comfortable and memorable.

Hotel Allegro

Whatever the Hotel Allegro is doing, other lodgings might want to take note. Everyone and their mother is checking in here: multi-generational ethnic families to attend reunions, spiky-haired European scenesters to sightsee, and suburbanites to see a Broadway-style show (the Allegro sits next door to the Cadillac Palace Theater).

The Drake Hotel

The ageless Drake is a regal majesty that has hosted real-life regal majesties such as Queen Elizabeth, among other glitterati, since opening its doors in 1920. The very quiet rooms are built like bank vaults, with marble baths and timeless styling.