It’s not a secret by now that Chicago is one of my favorite cities, if not my favorite city, in the States. Summertime Chi is enough to make you pack up your bags and relocate to the Windy City. But even though I’ve been to Chicago a handful of times, I had never been in the Winter, until I decided it would be a brilliant idea to bring in my NYE in this city notorious for its harsh winters with negative temperatures.

Let me first give this disclaimer, I’m from Texas. My winters usually involve days where shorts and sandals are appropriate, and even as I boarded my plane to head to temperatures slated to be at or around zero, I was only layered up to be prepared for disembarking from the plane. So, it’s not surprising that my conversation with my friend that’s a Chicago Native went something like this:

Me: Do I need to wear long johns and fleece tights at the same time?

Her: No.

Me: Are you going to help me decide the best way to tie my scarf?

Her: Yes.

Me: Do you think I need to go and get a ski mask?

Her: (I’m pretty sure this is probably where she slammed her hand to her forehead)

I’ve been to New York in the Winter, but that’s honestly where my experience with extreme cold weather temperatures comes to an end. And I can remember being so cold my first night in NY that I refused to leave the warmth of my cousin’s apartment. 110 degree weather, I have experience for days, but sleet and snow are outside of my realm of expertise.

There are a million ways to enjoy Chicago in the summertime. The weather is perfect, the festivals are in full swing, and the rooftop bars become every liquor connoisseurs playground. But what do you do when the temperature creeps into the negative, when it’s no longer fun to be an outdoor tourist, and when you’re in one of your favorite cities in the world?!?

Click here to get your Chicago City Pass for discounts to some of the most popular Chicago attractions.

Here is my list of 9 things to do in Chicago when the temperature tries to prevent you from living your best life:

Be festive. 

Thanksgiving, Christmas, and New Years are my favorite holidays, making winter and fall my favorite seasons to indulge in holiday activities.  Whether you go to ZooLights at Lincoln Park Zoo, see a Charlie Brown Christmas at the Broadway Playhouse, or visit the Magnificent Mile Light Festival, there is plenty to do for holiday enthusiast like myself.

Eat like you’re trying to gain a layer of flubber.

When it comes to food, Chicago is one of my favorite cities to restaurant hop and live the foodie life. This trip, I had the opportunity to enjoy some of Chicago’s best food outside of the ritzy and touristy areas. From the beef tips that I enjoyed at Wiley’s to the fried hot polish from Maxwells , I know that I put on a extra four or five pounds during my trip. I will just say that I needed the extra weight to battle the freezing temperatures. You can venture out on your own or take a food tour.

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Go ice-skating. 

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See a show on Broadway. 

Warm up with a cup of steamy hot chocolate.

There’s nothing like enjoying a warm, steamy mug of hot cocoa to escape from the frigid temperatures. Get on Trip Advisor and find the nearest highly ranked carrier in your area and forget it’s windy and below zero.

Visit a Museum. 

While many tourists know to visit the Art Institute Museum, Chicago is home to many other museums like the Field Museum or Museum of Contemporary Art.  Get a Chicago Explorer pass and escape the frigid temperatures to stimulate your artistic creativity.

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Go to a sports game. 

Whether it’s the Chicago Bulls, Bears, Cubs, White Sox etc, Chicago is the perfect city for sports fans. And if you like hockey, don’t forget to go and visit the all-new Black Hawks stadium.

Take a self-led tour of filming locations.

There have been many popular movies and TV shows filmed in Chicago. Since I’m a Batman fanatic, this is right up my alley. You can click here to track down some of Chicago’s most popular shot locations.

Shop at the new Jordan store. 

Picture Courtesy of Chicago Tribune

P.S.  If you would like assistance booking your next trip, click here.

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The first time I went to Chicago, I ended up back in Houston job searching and packing for a move to the Windy City. While the media likes to speak of Chicago’s murder rate and failing education system, the perfect summer weather, walking downtown, rooftop bars, and blue water beach often go unnoticed and unmentioned. But all that you have to do is look at the hashtag #summertimeChi to catch a glimpse of the Chicago that seems to be a secret from anyone that has yet to experience it.

Now, I’m not going to pretend that Chicago is all white picket fences and sunny skies, the gritty streets can sometimes be as hard as the harsh winters, but as with anywhere, your common sense should always prevail over your desire for adventure. Being that one of my friends is from Chicago, this trip I had the opportunity to actually spend a significant amount of my time on the West Side of Chicago. Yet, even with a glimpse into what is considered one of the roughest places in America, I still came home with a renewed interest in my Chicago job hunt and with the desire to pack my things and move, while I’m still unmarried and childless. 

I have never met anyone that has visited Chicago and not wanted to make it a place that they revisit frequently. My advice is to get a room near the Magnificent Mile or Downtown, due to their proximity to most of the popular eateries and tourist attractions, maximizing your time and inner city travel funds. The Tremont and Raffaello are 2 of my top picks for hotels on the Magnificent Mile that can usually be found at affordable rates, and if you plan on being a tourist, don’t forget to get a city pass for access and discounts to some of the cities most popular attractions. Gas and parking costs can be pricey in Chicago, making Uber, public transit, and walking more viable options than commuting across the city.

Below are a handful of things to make sure you add to your itinerary on your visit to Chicago:

Take a stroll down the Magnificent Mile

From Forever 21 to Gucci, the Magnificent Mile runs down Michigan Ave and is filled with stores, restaurants, and attractions.

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Go to Millennium Park and take a photo in front of The Bean

The infamous Bean in Millenium Park has to be one of Chicago’s biggest tourist magnets. Go ahead and get your perfect shot. It’s very social media appropriate.

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Indulge in the beauty of the Navy Pier

This trip was my first time visiting the Navy Pier, and I hate that I somehow missed it on my past visits. It’s the perfect place to just relax and unwind and maybe catch a bite at one of the restaurants while enjoying the view.

Go all the way up the Willis Tower

Even though the Willis Tower is still often referred to by its previous name, The Sears Tower, it was once the tallest building in the United States. After holding this title for 25 years, it was dropped down to second place following a new building at the World Trade Center site. For a fee, you can buy tickets to visit their Sky Deck for a view of Chicago from over 1300 feet in the air or book a lunch or dinner tour.

Channel your inner child at the FREE Lincoln Park Zoo

Being from Houston, I didn’t even know that zoo and free could be in the same sentence. Not only is the Lincoln Park Zoo ranked as one the best zoos in the world, but it’s also free to to the public. One of the best moments from my most recent trip to Chicago was having a family picnic on the grassy area near the zoo, something the kids with us have never experienced, and simply enjoying nature for a few minutes before our excursion through the zoo.

Take a 360 view from the John Hancock Center

Chicago seems to have an affinity for skyscrapers, and the John Hancock building  is no exceptions. In conjunction with offering 360 views from their observation deck, you can also heighten your sense of adventure, literally and figuratively, with their adrenaline pumping tilt experience. Imagine being 94 floors up and then being tilted over Michigan Avenue in a glass encasing. Horrifying right?!? Well, let’s just say I did it once, and while I found it electrifying, I only need to feel close to death once.

Eat Chicago Staples

Chicago is a city from a foodie’s dreams. From deep dish pizza to gourmet hot dogs and Italian beef sandwiches, make sure you save up your calories. And if you want to see what all of the buzz is about stop by Giordanos, Portillos, and Home Run Inn. Remember, calories don’t matter in Chicago. Resume your diet when you get back home. This Chicago food tour is another great option for foodies.

Visit a Rooftop Bar

There are 2 cities that should be in the record books for the best rooftop bars, DC, and of course, Chicago. One of our days was spent simply rooftop hopping, and there was not one that let us down. From the signature cocktails to the banging DJs, here are some of my favorite Chicago rooftop bars:

Joy District



ROOF on the Wit

A specialty cocktail from Apogee

A specialty cocktail from Apogee

Sidenote: And if you’re looking for a beach party, go ahead and add Castaways to your list.

Attend a Basketball or Baseball Game

Whether it’s the Chicago Bulls, Cubs, or White Sox, if you have time and the season prevails, catch a game for any of these legendary teams. And if basketball or baseball are not your thing, or you’re just loyal to your home team, at least take a drive by the stadiums.

Sidenote: The Michael Jordan statue has been moved inside of the United Center, so it’s not as easy to snap a quick photo in front of this legend anymore.

See a show at the Chicago Theatre

Built in 1921, this legendary theatre, once dubbed the “Wonder Theatre of the World, still hosts a variety of different shows, from traditional theater to comedy. Click here to check out their calendar of events.

Go to the beach

When I tell people that Chicago has a real beach, I’m often met with either a blank stare or a “yeah right” face. But just in case you don’t believe me, here you go. So grab your swimsuit, and take a plunge into the frigid water.

This picture was taken from

This picture was taken from

Take a river cruise

The view from land is great and all, but the view from the water is even better. As you cruise the Chicago River, you will be given a brief run-down of Chicago’s colorful history. Click here to secure your spot on the highly recommended Chicago architecture river cruise.

Fun Fact: For St. Patty’s Day the Chicago River is dyed green. Being this is my favorite holiday, I’m still sad I haven’t had a chance to make it to join in the festivities yet.

Feast at the Taste of Chicago

Every year, Chicago hosts the Taste of Chicago, showcasing some of their best restaurants and city staples. This was my first time going, and the food was sooooo good. It was also my first time tasting an Italian Beef sandwich. I’ve been to many festivals, and the best thing about this festival is that it wasn’t overpriced. For $20, I received 28 tickets, and even though I ate like it was my last supper, I still walked away with leftover tickets (which I donated to the family pot for a huge funnel cake). Another options for foodies is embarking on a Chicago food tour.

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And last but not least, if you will be in Chicago for several days and want discount pricing on some of the popular tourist locations and skip the line access, consider purchasing the Chicago City Pass or securing a spot on the Chicago hop-on hop-off bus.

P.S. If you would like help planning your next vacation, click here.

Disclaimer: Some of the links in this blog are affiliate links, meaning at no additional cost to you, I will earn a commission if you click through and make a purchase.