Last Updated on 01/09/26 by Rose Palmer
Chicago winters get a bad rap. Yes, Chicago is called the “Windy City” for a reason, and winters there do still get snowy and cold. But like everywhere else in the world, global warming has had its impact here as well, and Chicago winters are nowhere near as frigid as they were when I grew up there in the 70’s and 80’s.
If you are looking to visit Chicago on a budget, then consider a winter weekend break in my favorite city as your best option.
I grew up in Chicago, went to school and college there, and got married there. Unfortunately, more schooling and a career took me away. Since I left, my travels have taken me to many wonderful cities across the globe that I loved and that I would be happy to return to, but Chicago will always remain my first love.
Chicago in Winter
This is the view of Chicago that I grew up withI am clearly not the only one who thinks this is a great Midwest location to visit – the number of annual tourists has grown to almost 60 million. That’s 20 times as many tourists as there are residents in this, the third-largest city in the US. This popularity means that visiting Chicago during the prime tourism warm weather months can get pricey.
I still visit Chicago 1-2 times a year and have gone during all seasons. Maybe it’s because I grew up there, but I like Chicago in the winter. While many people shy away from a midwinter visit, I really enjoyed my recent winter trips, especially because it was very easy on the pocketbook. Plus, there were a lot of things to do in Chicago in the winter.
Ideas for visiting Chicago on a budget
Since Chicago is not typically a midwinter destination, my airfare was significantly less expensive than at any other time of year. And with a flexible schedule, midweek flight rates were even less expensive.
I also look at flights going into Midway airport as well as the megasized O’Hare. And I don’t hesitate to consider a one-way flight option, going into one airport and flying out the other. I like to use the Skyscanner site to find my best flight choices.
Besides airfare, hotel costs are also a major expense when traveling. Chicago has a lot of amazing hotels, which get very pricey during prime tourist season. But if there is a specific hotel I’ve always wanted to try, I will be able to indulge at a much lower rate in the middle of winter.
I’ve stayed at the Hilton Magnificent Mile Suites, where for as low as $125 a night. I had a modern suite with a bedroom, sitting room, a large bathroom, and views of Lake Michigan. I was a block away from the Magnificent Mile and the John Hancock Building and three blocks from the subway station. Any other time of year, I would have paid at least two or three times that price for this room.
And speaking of subway stations, that is another easy way to save money touring in the city. The blue subway line took me directly from O’Hare airport to downtown Chicago for $5.00. With my tap and pay credit card, I didn’t even have to bother going through the process of buying a ticket.
In 2014, Chicago’s blue subway line underwent a $492 million restoration, which has produced modern, clean, and well-lit stations with up escalators, elevators, and handicap accessibility.
Other subway lines have also undergone modernization, which makes the $2.50 single ride ticket not just an inexpensive way to get around the city, but also a pleasant one as well. I use the CTA’s visitor information site to plan my trip to my favorite Chicago attractions.
Like other cities, Chicago also hosts restaurant week at the end of Jan. and into early February. With hundreds of restaurants participating, this is a good and less expensive way to try some of the many ethnic eateries throughout town.
Chicago has always been a city of neighborhoods, with many neighborhoods having a particular ethnic flair. I can have saganaki in Greek Town, real Chinese food in Chinatown, or homemade Polish pierogis in Portage Park.
I definitely do not leave the city without trying one of the deep-dish pizzas. Chicagoans will argue over their favorite, but I can’t say I’ve ever had a Chicago-style pizza that I did not like. I’ve eaten at Giordano’s many times, and I don’t think you can go wrong with the original Uno’s or Due’s in downtown.
One of my favorite things to do in Chicago is to walk or bike along the lakeshore, but this is not something I recommend in the winter. However, many of the best things to do in the city are indoors, which makes them perfect Chicago winter activities when the weather is blustery. The Chicago CityPASS was a good way to save money on entrance fees when I was planning on visiting the most popular museums and sights.
With my Chicago CityPASS, I saved about 50% off individual ticket prices to my favorite museums. The pass covered the entrance fee to five attractions – the Shedd Aquarium, the Skydeck at the Willis Tower, and a choice of three from the following: the Field Museum, the Adler Planetarium, the Art Institute of Chicago, the Museum of Science and Industry, the 360 CHICAGO Observation Deck at the John Hancock Building, and Shoreline Sightseeing Architecture tour.
The advantage of visiting these popular Chicago attractions in winter is that they are not full of tourists. I enjoyed the exhibits alongside the locals. I could take my time staring at the many Monet paintings at the Art Institute or watch the fish get fed by a diver in the Caribbean reef tank at the Shedd Aquarium.
After visiting the Museum of Science and Industry with my CityPASS, I did not pass up the opportunity to see the sunset views of the city from my favorite skyscraper, the John Hancock Building.
Chicago may be called the Second City when it comes to comedy, but it is top-notch with regard to theater, art, and concerts. The city draws in the top touring Broadway productions, but at a fraction of the cost of seeing the same show on Broadway. When Hamilton was still playing in Chicago, I was able to get last-minute tickets for about $150. Good luck even finding a ticket to that show in NY City, much less at that price.
Chicago is also home to the blues, and my favorite spot to listen to blues music is Buddy Guys Legends Bar. Lunch and dinner come with a free acoustic show. After dinner, I stay for a nightly performance by top blues artists for a minor admission fee.
Winter also doesn’t get in the way of celebrating festivals and events in Chicago either. There is some type of special event going on every weekend. I look at Time Out Chicago to find out what’s going on in the city when I am there.
When I visited one February weekend, it coincided with the Chinese New Year celebration and parade. It was unseasonably warm, so there was a large turnout to watch marching bands, decorated floats, and lots of dancing Chinese dragons. And only in Chicago would you have a Scottish band in kilts and playing bagpipes performing at the Chinese New Year parade.
If the weather is favorable, I also take the time to discover some of Chicago’s amazing free public art scattered throughout the downtown area. The first non-commemorative sculpture, “The Picasso”, was installed in 1967. In 1978, the Chicago City Council passed an ordinance that “a percentage of the cost of constructing or renovating municipal buildings be set aside for the commission or purchase of artworks.”
As I stroll through downtown’s world-class architecture, I also get to experience world-class art by names like Chagall, Miro, and Anish Kapoor, who designed the “Cloud Gate” (better known as The Bean) in Millennium Park.
For other ideas on what to see and do on my Chicago visits, I peruse the Choose Chicago tourism board website for a complete list of performances, activities, and special events, especially in the individual neighborhoods.
My very biased opinion is that Chicago is the best city to visit any time of year. Whether it’s for a week or a quick weekend trip to Chicago, its beautiful green lakefront, interesting art and architecture, and world-class museums and restaurants make it a destination that can be enjoyed year-round.
But when I am looking to see the city sights and save some money at the same time, then I consider a winter break in my favorite city.
Please note that I received a complimentary Chicago CityPASS. All content and opinions are my own.
Other related posts about Chicago and the Midwest:
Things to do in Chicago: My Favorite 25 Things to Do In Chicago Like a Local
Where to find the best Chicago street art: The Best Chicago Street Art – Finding Murals, Sculptures and Other Public Art in the Windy City
Discover scenic southern Illinois: There’s a Little Bit of Paradise in the Garden of the Gods, Illinois
See the artsy side of Indianapolis: Discovering Artistic Indianapolis – My Favorite Things to Do in Indy
Thanks for visiting.
Rose
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