Despite unpredictable weather and often chilly temperatures, winter can be a great time to travel to Chicago. However, it also takes a bit of preparation to make sure your trip goes smoothly. Here are a few Chicago winter travel tips to keep in mind ... 

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Certiļ¬ed reviews by travelers like you.

5 star rating: Highly Recommended
August 2015

Every thing was wonderful on this trip, even the weather! Your staff were very friendly and helpfull.
Just one thing, the staff on board th boat should let people know what side is the best side to sit on
to get the best view of what they are going to talk about.

Doing what: Lake Michigan Sightseeing Cruise

5 star rating: Highly Recommended
August 2015

Great way to see the city. Neighborhood tours are a nice addition to the city loop tour. Drivers and guides are friendly knowledgeable and professional.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

A good experience. The guides had a lot of good information for out of City visitors. I had lived 57 years just 30 miles away and was in and out of the city during those years. But it was very good for my 18 year old grandson who had never been to Chicago.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

Learned so much about the city, and the tourist guides were very funny and accommodating. saves a lot of money from cabs and ubers

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

This was actually more than we expected! It was not just hop-on-hop-off, you had a tour guide on the bus who pointed out interesting things along the way. This is a great way to see some of the downtown area!

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

Great way to see a lot of the city in a relatively short amount of time. Our tour guide was very knowledgeable and made the experience so much better. We did not get off so we could continue to hear her talk about the architecture and the great city of Chicago! Really a must do. I used to live in Chicago and I learned a lot!

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

Great tour if you are short on time.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

We loved traveling about on the tour. The first time round we just went from beginning to end to see where we would be interested in getting off. Our guide was entreating as well as informative. I always enjoy learning about the areas I am traveling in. The frequency of buses was a bonus and the areas of stopping was worthwhile. I would definitely use this service again.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

This is the way to see the city! It was a day that rained on and off so we were out of the weather when we wanted to be. Nice clean double decker buses give you that option. Very good guides. Helpful, courteous and friendly. Great way to see a lot of the city in a short period of time

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

I live in Chicago and I learned some things that I didn't know. I highly recommend this tour.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

Great way to see the sights and get around key locations. Guides are friendly and knowledgeable and the buses run regularly up until 5, plus there is a night tour with limited stops.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

absolutely the best way to see Chicago - easy to get to places we wanted to see. Staff were very friendly and helpful with our questions!

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

My daughter and I took 3 of the Chicago City Hop on Hop Off tours and they were fabulous!!
This is the original city tour and was informative, fun and just perfect for our first time.
Thank you so much.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
August 2015

It was excellent.
Never thought it could be so much good.
More important Business is very fair. We could get the refund very easily and quickly of our night tour which we cancelled as it was already available in our booking.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
July 2015

It was very educational and the views was great!

Doing what: Lake Michigan Sightseeing Cruise

5 star rating: Highly Recommended
July 2015

A great way to see the city. Easily located stops throughout Chicago, wonderful guides and lots of flexible touring options.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
July 2015

Handled well and efficiently. Good tour. Would recommend to others and friends. No negative experiences relative to the whole tour.

Doing what: Lake Michigan Sightseeing Cruise

5 star rating: Highly Recommended
July 2015

The bus ride was the best ever. My son and I had the time of our lives. The guides were the best! He and she gave us information about Chicago we never knew. I Highly recommend this tour to anyone wanting to learn about Chicago.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
July 2015

It was a wonderful view of not only Lake Michigan but the city of Chicago from Lake Michigan - one word of advice - do NOT go on a cool day - makes for an uncomfortable boat trip otherwise Fantastic!!!

Doing what: Lake Michigan Sightseeing Cruise

5 star rating: Highly Recommended
July 2015

We did the two day tour. Both days were excellent. Frank the guide did an excellent job.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
July 2015

Great itenary and supplying plastic smocks during brief rain shower was a great idea by your tour operator

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
July 2015

Every tour guide was terrific. Never waited more than 5 minutes for a bus. Saw everything and enjoyed the beautiful city.Loved the free shirt and chocolate bars and popcorn. Used this site for SanFrancisco and had the same great experience.Thank you.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
July 2015

Tour Guide Chris was SMART, Funny and super knowledgable about Chicago and history. He made the tour so enjoyable. Well done!

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
July 2015

A very informative tour with great knowledgeable tour guides who made the trip fun as well as giving lots of tip and ideas. well worth doing and we were so pleased we did this at the start of our adventure in Chicago.

Doing what: Chicago City Hop-on Hop-off Tour

5 star rating: Highly Recommended
July 2015

On the first day of our two day pass, it was unseasonably cold and very rainy so everyone sat inside the bus which made it next to impossible to see the buildings. On the second day, the weather was perfect. The guide was knowledgeable, well spoken and passionate about Chicago. Highly recommended.

Doing what: Chicago City Hop-on Hop-off Tour

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