One Day in Chicago: Top 5 Things to Do & See

Top 5 best things to do if you only have one day in Chicago featured by top US family travel blog, More than Main Street.

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A Day in Chicago

Only have one day in Chicago? No worries! We can help!

Chicago is a super fun city deserving of a spot on your USA bucket list! There are so many fun things to do and see in Chicago but sometimes we can only fit one day into our travel plans. I get it. We can relate. One day is better than none!

My best advice if you only have a day in Chicago? Spoiler alert: It’s pretty much my same advice for visiting any city or destination. Plan as much as possible and then enjoy the experience. Be present and grateful for the amazing opportunity to explore somewhere new! Don’t stress or worry that you didn’t make it to see everything. Hey…that gives you a reason to go back, right?

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How to get to Chicago

Chicago has two major airports: Chicago O’Hare International (ORD) and Chicago Midway Airport (MDW). Both airports are conveniently located with easy access to the city. Bus service, taxi, Uber, Lyft, and rental cars are all available from both airports.

How to get around Chicago

Our preferred way to get around Chicago is by Uber or just walking. We have found Uber is just so affordable and easy to use in cities. During our last visit we did have a rental car. Finding parking was doable but difficult since we had a large SUV that did not fit the height clearance in many of the public garages. While we did finally find an open air parking lot, it was not cheap, and not necessarily convenient to the attractions you want to see.

Top 5 best things to do if you only have one day in Chicago featured by top US family travel blog, More than Main Street.
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One Day Chicago Itinerary

It’s always so hard to choose what to do when you only have one day…here’s what we suggest for Chicago in 24 hours:

  • The Magnificent Mile
  • The Bean (AKA Cloudgate) & Millennium Park
  • The Chicago Arhcitechure Foundation Center River Cruise
  • The Skydeck Ledge at Willis Tower
  • Eat! Food is such a fun part of visiting a city…so indulge yourself and try all the classic Chicago foods.
Top 5 best things to do if you only have one day in Chicago featured by top US family travel blog, More than Main Street.
The famous Chicago sign is about two blocks off of the Magnificent Mile.

The Magnificent Mile

The Magnificent Mile is the 13 block stretch of Michigan Ave and the “center of it all” in Chicago. While many would consider this touristy, I still feel like it’s a must to do at least once. Peruse the over 400 stores from the high end big name brands to the small super cute boutiques, stroll, and just soak up the city.

Trying to decide where to stay in Chicago? We loved our stay at the Fairfield Inn & Suites Chicago Downtown/ Magnificent Mile. This was possibly the nicest, most modern Fairfield Inn we’ve ever stayed in PLUS it’s the best location right near the Magnificent Mile.

The Bean (AKA Cloudgate) at Millenium Park is a must see Chicago attraction.
The Bean (AKA Cloudgate) at Millennium Park is a must see Chicago attraction.

The Bean & Millennium Park

Start your day walking the Magnificent Mile down to Millennium Park. Take time to check out the Bean (Cloudgate), one of Chicago’s most popular and recognizable tourist attractions in Millennium Park. Another must see in Chicago is the Crown Fountain. Two giant 50 foot LED screens display changing faces of Chicago residents. It’s fascinating to say the least!

Next up explore Millennium Park, the BP Pedestrian Bridge, and Maggie Daley Park. Make sure if you’re visiting Chicago with kids you plan extra time here as they won’t want to leave Maggie Daley Park! Best part of your day so far…these are all free things to do in Chicago!! Woot woot!

ProTip: The Bean can get super crowded so plan accordingly. Even in my photo above there were quite a few people there and it was raining!!

The Architectural River Cruise

Next on your agenda is The Chicago Architecture Foundation Center River Cruise on Chicago’s First Lady. Now, I was a bit hesitant about doing this to be honest. I mean I can’t say architecture or history are of huge interest to me. But everyone we talked to said how fantastic it was and it was a must do activity in Chicago. Well…everyone was right!! My husband and I both agreed, it was fantastic. We loved the 90 minute river cruise and now we recommend it to everyone we know!

The do have snacks, drinks, and cocktails available, but I’d recommend grabbing lunch after your cruise before you head over to the Skydeck Ledge!

The Skydeck Ledge at Willis Tower is a must see in Chicago!
The Skydeck Ledge at Willis Tower is a must see in Chicago!
The Skydeck Ledge at Willis Tower is a must see in Chicago!
The Skydeck Ledge at Willis Tower is a must see in Chicago!

The Skydeck Ledge at Willis Tower

Visiting Chicago with teens? One of the best things to do in Chicago with teens and tweens is visit the Skydeck Ledge at Willis Tower. This is the ONLY thing my teen asked to do during our visit to Chicago. (Doing it for the gram!!) But in all honesty, our whole family enjoyed the experience. The views of the city are amazing and the Ledge is kinda cool and kinda scary at the same time.

Know Before You Go: Visiting the tallest building in the western hemisphere is cool and all but I always like to manage expectations. There will be a line although it does move pretty fast. But they literally give you 60 seconds on the actual ledge if you’re a group of three or less and 90 seconds if you’re a group of four or more. The set a timer and everything. So you have to be quick. They let our family of four have the entire space but if you were only a group of two you had to share the space with another couple. They of course have a photographer to sell you a photo but you are allowed to take your own photos. Expect one to two hours here.

If you only have a day in Chicago you must try a Chicago style hot dog from Portillo's. (Featured by top US family travel blog, More than Main Street)
A famous Chicago style hot dog from Portillo’s.

EAT! Indulge all your foodie desires in Chicago!

There are just certain foods you HAVE to try when you visit Chicago. While you may love or hate them, you have to try them. Here are our top picks to round out your Chicago itinerary:

  • Chicago style hot dog– Everyone said you have to go to Portillo’s…so we went to Portillo’s. We were a little confused at first, it’s kind of like a cafeteria, but luckily some very kind employees helped us out. Our opinion…it was OK, but not all the rage. I know, I know, that’s an unpopular opinion, but that’s just the truth.
  • Garrett’s Popcorn– True story: during our first visit to Chicago we noticed this huge line at a store across from our hotel. Of course we had to see what all the fuss was about. Turned out to be Garrett’s popcorn…well worth the wait…and if it was open…there was usually a line!
  • Do-Rite’s Donuts & Chicken– we pretty loyal Yelp users as it almost never lets us down. We found Do-Rites tucked away in this tiny corner near our hotel during our first visit and we became instant fans. Bonus: There’s one in the Willis Tower now too. You can visit the Skydeck Ledge and have Do-Rite’s all in one fell swoop!
  • Chicago style pizza– We’ve tried two of the most popular spots: Giordano’s and Lou Malnati’s. They were both good (again with the unpopular opinion) but not blow your mind amazing. I think we just like some other styles better. A couple of tips: these restaurants can be super busy!! Our hotel actually gave us a voucher to skip the line at Giordano’s which saved us waiting over an hour for dinner! YAY! Also these slices of pizza are so much heavier and thicker than you may be used to so consider this when ordering an entire pizza. You may not be able to eat as much as you think you can.
  • Ice Cream! I mean who doesn’t love a sweet treat on vacation? And Chicago is guaranteed to deliver some of the best ice cream around!
  • Frontera Grill– Ok so I just had to go here because I’m a huge fan of the TV show Top Chef and I’m obsessed with mexican food. So I was dying to try Rick Bayless’ flagship restaurant, Frontera Grill, in Chicago. Needless to say we were fans!! The food was amazing, the margaritas were to die for, and hey Rick Bayless was literally sitting at the bar eating with his wife. How cool is that??
  • Have a little extra time? Get to sample even more popular spots with a Chicago food tour!

Have Two Days in Chicago or More?

If you happen to have two days in Chicago or more, here are our top suggestions for more fun things to do in the city:

  • Visit Navy Pier– this is always a hit with the kids! Don’t miss the Centennial Wheel.
  • Go to a Cubs game at Wrigley Field! You can’t get a more authentic “Chicago” experience than this! We got lucky and were able to see a playoff game during one of our visits.
  • Chicago’s Lakefront Trail- PRO TIP: Wear good walking shoes (unlike me!) to explore this beautiful 18 mile paved trail along Lake Michigan!
  • Take a Big Bus tour.
  • Catch a comedy show. Did you know Chicago is known for comedy? We were able to grab last minute tickets to see an improv show at Second City, which was worth every penny.
  • Plan date night at The Aviary. Ok…so only add this to the Chicago itinerary if you’re visiting without kids. But this may be the swankiest thing we’ve ever done! Legit…you have to book reservations and they make alcohol an experience to remember. (Just be careful- the drink are strong and this isn’t a cheap affair!)
  • Get inspired by a visit to Chicago’s #1 museum: The Art Institute.
  • Say Hi to the beluga whales a the Shedd Aquarium.
  • Want more views? Check out 360 Chicago.

What to See in Chicago

Whether you’re visiting Chicago with kids, your partner, or solo, no doubt you will be able to find more than enough to fill your day! I hope this helps give you an idea of some of the must see attractions so you can tailor your Chicago itinerary to meet your needs!

Have you been to Chicago? What would you list as absolute must do activities if you only have one day in Chicago? Let me know in the comments below!

Top 5 best things to do if you only have one day in Chicago featured by top US family travel blog, More than Main Street.
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  1. Only a single day in a city as great as Chicago is such a challenge – but you’ve managed to hit the highlights! I personally don’t love and would skip the glass viewpoint of the city — I am scared of heights — and would go to a museum instead. I adore the Field Museum!

  2. This looks like so much fun! Marty has family in Chicago so he has been several times but I have yet to make it. I need to change that. I need my picture in front of The Bean! LOL!

  3. As much as I want to say it’s the sites of Chicago that make me want to visit, after reading about all those great food spots I think it’s more that haah! They sound so yum! Looks like a really cool city and I look forward to going one day!

  4. These are all great picks! I was only in Chicago for half a day or so, but managed to check out several of the places you mentioned–I really want to do the architecture tour next time!

  5. You’re totally spot-on! This IS the perfect 1-day Itinerary for Chicago! …Seeing your photos and hearing your stories just makes me want to go back to this beautiful city! Great post!

  6. Some great ideas for if I go back to Chicago. I went a few years back on a business trip and spent an extra couple days. It was January though so really cold. I didn’t love the deep dish pizza, especially trying to finish one on my own. But the city itself was such a great place

  7. Ahh, you got all the iconic shots, from the Bean to the river! I went to Chicago many, many years ago, and my memories are hazy, but you’re bringing back some of the exciting vibes I felt.

  8. Wow, this post really makes me want to go back to Chicago. We loved the architectural river cruise and I agree with your (unpopular) opinion on Giordano’s 🙂 Next time we will have to try the Skyledge and I’m also dying to try Portillo’s! Thanks for all the great recommendations.

  9. Something to go in Chicago without the kids is to hit some of the legendary jazz nightclubs after dark. The live shows I’ve been fortunate enough to walk into have been worth the late night!