Chicago on a Budget – A Winter Weekend Break in My Favorite City

How to visit Chicago on a budget

Last Updated on 03/03/21 by quiltripping

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.

This is the view of Chicago that I grew up with

I 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 becasue 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 February trip, especially because it was very easy on the pocketbook. Plus, there are 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 any other time of year. And if your schedule is flexible, midweek flight rates are usually less expensive also. Make sure to also look at flights going into Midway airport as well as the megasized O’Hare. And 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.

Chicago skyline view from the Shedd Aquarium

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 you’ve always wanted to try you will be able to indulge at a much lower rate in the middle of winter.

This trip I stayed at the Hilton Magnificent Mile Suites where for a $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 twice that price for this room.

Loved staying at a hotel that was only a couple of blocks from this view

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 a s well. Use the CTA’s visitor information site to plan your trip to Chicago attractions.

The Chicago Transit System makes it easy to get around

Like other cities, Chicago also hosts restaurant week at the end of Jan. and into early Feb. 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. You can have saganaki in Greek Town, real Chinese food in Chinatown or homemade Polish pierogis in Portage Park.

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 I did not like. I’ve eaten at Giordano’s a number of times and I don’t think you can go wrong with the original Uno’s or Due’s in downtown.

Deep dish pizza at Giordano’s

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 is a good way to save money on entrance fees if you are 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 covers the entrance fee to five attractions: the Field Museum, the Shedd Aquarium, the Skydeck at the Willis Tower, a choice between the Adler Planetarium or the Art Institute of Chicago and a choice between the Museum of Science and Industry or  the 360 CHICAGO Observation Deck at the John Hancock Building.

Use the Chicago CityPASS to save money on the major Chicago attractions like the Willis Tower Skydeck

The advantage to visiting these popular Chicago attractions in winter is that they are not full of tourists. You’ll be enjoying the exhibits along with the locals. You can take your 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 building, the John Hancock Building. Rather than pay to go to the observation deck, I prefer to pay for a drink instead at the Signature Lounge on the 96th floor. The drink comes with comfortable and stunning views in all directions. And for the ladies, the worst kept secret is the view from the lady’s bathroom which is a popular selfie spot.

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 comes with a free acoustic show. After dinner 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.

Chinese Newr Year parade in Chicago's Chinatown
Chinese New Year parade in Chicago’s Chinatown

The February weekend that I recently visited 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, 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”.

Alexander Calder’s Flamingo sculpture in Chicago’s Federal Center Plaza

As you stroll through downtown’s world class architecture you’ll 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.

Chicago's Cloud Gate sculpture
The Cloud Gate sculpture in Millennium Park

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 if you are looking to see the city sights and save some money, then consider a winter break in my favorite city.

If you have more than just a couple of days, check out my list of 25 things to do in Chicago.

Please note that I received a complimentary Chicago CityPASS. All content and opinions are my own.

You can see more of my CHICAGO CHINESE NEW YEAR PARADE web story and my BEST OF CHICAGO ON A BUDGET web story.


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