Things to Do in Chicago: 3 Day Itinerary for the Windy City

There are so many amazing things to do in Chicago because it has so much to offer! We think this itinerary is a great start to figuring out what to do while you spend some time in the Windy City. If you’re staying longer than three days or this itinerary isn’t your cup of tea, we’ve included 10 other great things to do in Chicago at the bottom of this post.

Our trip took place in May and we planned on a little warmer weather as Chicago’s summer was quickly approaching. However, being near Lake Michigan can be really cold so be prepared! We were not…

Getting to Chicago

First off, let’s talk about getting to Chicago. Google Flights is your best friend. If you’re too far to drive or if you just prefer the air, then Google Flights! Read our post on how find cheap flights using Google Flights and never look back!

In our case, we love a good road trip. Coming from Oklahoma City, our drive was around 12 hours. The best part about this road trip is that we took old Route 66 when feasible. It turns out Route 66 is mostly just the modern day interstate 44 so it’s nothing too special. Although there are a few exits that have some attractions along the way so keep an eye out if you’re lucky enough to take this route!

Things to do on Route 66: Visit Uranus

We got a little antsy around hour 9, after we found a slow leak in our tire and had it patched in Springfield, Illinois. It’s never fun to waste time on a detour for a leaky tire, but it was cool to see where President Lincoln lived!

Night came and we thought Chicago was over the next hill so Darah played Frank Sinatra’s Chicago…but unfortunately just a little too early. Alas, we could finally see Chicago on the horizon, wonderfully alight in the distance.

After some heavy traffic we arrived at our Airbnb and began our great Chicago adventure!

To save money and have a more relaxed time, we decided to stay a little outside of downtown. Our Airbnb was in Logan Square, a trendy neighborhood northwest of downtown with so many great restaurants and bars (another reason we chose this Airbnb).

Logan Square is a great place to stay when looking for things to do in Chicago

If you end up staying outside the downtown Chicago area then we recommend Lyft or Uber or a taxi as means to get around. We used all three on this trip. There’s always the historic Chicago “L” metro, which can take you practically anywhere. Just depends on your plans and personal preference!

Chicago Explorer Pass and CityPASS

Next, let’s talk about the coolest thing about Chicago: the attraction passes!

There are a couple options for attraction passes, like the Go City Card: Chicago Explorer Pass which is what we got, and CityPASS. These are essentially the same idea: you pay an upfront amount and get to see a number of attractions throughout the city. And there is SO MUCH to see! Check out the Chicago Explorer Pass.

We did the math and it’s a money saver for sure. So if you’re going to museums, zoos, the observation decks, or any other Chicago attractions then make sure to check this out online before you go! We bought ours on Groupon and chose the 3 attraction pass. It was the cheaper option and we were moving abroad to Taiwan in three months so we had to be a little budget conscious! But man, we really wanted that 5 attraction pass.

Okay, now for some things to do in Chicago!

Day 1: Art Institute of Chicago and Exploring

The Art Institute of Chicago is a must-see museum and you can use your attraction pass! It features art from many different periods and all around the world, including the largest collection of impressionist paintings outside of the Louvre. They have many famous paintings like Water Lilies by Claude Monet, A Sunday on La Grande Jatte by Georges Seurat and American Gothic by Grant Wood (unfortunately it was on loan when we visited). There’s Renaissance art, tons of portraits, medieval armor and weapons, and so much more. You could spend all day in this museum if you really wanted.

Things to do in Chicago: Visit the Art Institute of Chicago
Photo by: TonyTheTiger at English Wikipedia

The Art Institute was exhausting, so it was the perfect opportunity to grab a late lunch! There are so many eateries around the museum, take your pick! Unfortunately, we were too hungry to look into what the best place to eat would be so we just walked into the first restaurant we saw. We’ve heard great things about Russian Tea Time and Oasis Cafe, a Mediterranean restaurant you can find by walking through a jewelry store on Wabash.

The museum is also next to Millennium Park, which houses the famous Bean. This makes for a great breath of fresh air after being inside all morning.

Seeing the Bean and surrounding parks is one of the best things to do in Chicago

Like most major US cities, every district seems to be packed with restaurants and bars. Logan Square, where we stayed in an Airbnb, was no different. There were even a couple local breweries in this area. If you have a chance to eat/drink at Revolution Brewing then take it! The beer is really good and the menu and atmosphere make for a great night out. If craft beer isn’t your thing and you love Italian food then Buona Terra is a must! Their ravioli stuffed with veal is divine.

Day 2: Brookfield Zoo, Deep Dish Pizza, and Shakespeare on the Pier!

If you’re like us then you love going to Zoos. We’ve now been to Chicago’s, Taipei’s, Colorado Springs, Oklahoma City, Tulsa, Houston and there are many more to come! Brookfield Zoo Chicago was one of our favorites! Mainly because the two bears wrestling in the pool made our day! This zoo was well-maintained and a lot of fun. It was easy to get to since it’s also a little outside of the city and we had our car.

Things to do in Chicago: See bears at Brookfield Zoo

If Brookfield is too inconvenient to get to, there’s also Lincoln Park zoo, more centrally located and free to the public. But we read that Brookfield is better, plus it was included in our attraction pass. We haven’t been to Lincoln Zoo yet so we can’t be the judge, but you have your pick between the two!

Lunch didn’t happen until 4pm so we were starving. We ate the food that comes to everyone’s mind when Chicago’s on the brain: deep dish pizza. Pequod’s Pizza is where it’s at. A very cool atmosphere decked out in Cubs and Blackhawks memorabilia and dim lit with brick wall interior, this is the perfect joint to have a cold one and chow down on some deliciously cheesy deep dish pizza. We had the pepperoni with garlic and mushrooms.

Things to do in Chicago: Eat deep dish pizza from Pequod's

Writing this post from Thailand, we realize how much we miss pizza…

Shakespeare on the Pier takes place at the Chicago Shakespeare Theater, literally on the Navy Pier. We had the chance to see Macbeth, a darker Shakespeare play, but nonetheless a great show at an awesome location.

The best part about this theater is they offer a discount to people under the age of 35. You can buy up to 2 tickets for $20 each (so you can bring an older than 35 guest with you). Normally tickets can be $48 or more so this is a great deal! Be sure to check the calendar ahead of time because Shakespeare isn’t always showing. There are breaks between Shakespeare plays where other performances take place.

Afterward was the perfect time to hang out and end the night at a bar. The Navy Pier is a very popular area so your options are endless. We decided to head back to Logan Square and have a relaxing night cap there.

Things to do in Chicago: Visit Navy Pier

Day 3: Adler Planetarium, A Walk in the Park, The Purple Pig, Magnificent Mile and More Italian…

If museums are your thing then you have to go to Adler Planetarium when in Chicago. This museum is situated next to Lake Michigan and has fantastic views of the cityscape, as well as the lake itself. It was quite foggy the morning we visited so Chicago’s buildings were hiding for a few hours, but it gave the city a kind of cool, ominous look.

The planetarium was a lot of fun, with great shows that take you through our solar system and to deep space, as well as tons of exhibits talking about all things space. The dome movie theater at Adler didn’t quite match Hayden Planetarium in New York City, but it was still worth checking out. And it’s part of your attraction pass!

Things to do in Chicago: Visit Adler Planetarium

This day was arguably our favorite day because after the planetarium, the day was ours to do what we do best: walk around aimlessly and explore. We did just this on our 2 day journey in NYC, where we walked 23 miles in two days!

While we didn’t quite walk a marathon in Chicago, we walked A LOT. We began by leaving the planetarium and heading for Grant Park and Buckingham Fountain. But first, we had to have a cheesy chili dog from a street vendor for a few bucks. One of the best foods we tried in Chicago. If you see a hot dog stand then do yourself a favor and grab one. Or two.

Things to Do in Chicago: Gaze at Lake Michigan from Adler Planetarium

Bordering Lake Michigan, Chicago has so many beautiful parks and plazas, you don’t even realize you’re in a huge city. Until you turn to your left and see skyscraper after skyscraper.

Buckingham fountain is one of the many fun things to do in Chicago

Buckingham Fountain is a great place to stop and relax and even people watch, and the Bean is just a short walk north from there. At this point our attraction pass was spent and it was overcast, hindering a trip to 360 Chicago Observation or Skydeck Observation. These seem like cool experiences, but we’ll have to check them out during our next visit. If you’re not into planetariums, it might be a good idea to try one of the observation decks instead.

Things to do in Chicago: Visit Navy Pier on Lake Michigan
By David Bjorgen

We ended up walking from the planetarium to Navy Pier, and from there we went to the Purple Pig for lunch. This restaurant is not budget friendly, but it is so worth it. We hope you get to try it. After a lengthy wait (which is a great opportunity to walk the magnificent mile), you’re seated at large tables next to other groups, so don’t be afraid to be social. We had chorizo stuffed olives, chicken thigh kabobs, and 7 year cheddar cheese. The restaurant also has great views of Chicago’s architecture. Make sure to eat here if you can!

The magnificent mile is fun to walk, with its many street performers, shops and delicious food. We’re not really into brand name shopping but we did stop in the multi-story H&M and Dylan’s Candy Bar, where we stocked up on a few pounds of sugar to carry with us on our adventure.

We walked around even more, hitting up State Street (from Frank Sinatra’s song) and practically taking our own architecture tour without the guide. Tulips were in bloom and it seemed that every building wanted in on the action. Tulips were everywhere, which was alright with us.

Try walking the magnificent mile when looking for things to do in Chicago and see the tulips!

After working up another appetite, or rather forcing another appetite, we went to Volare for some Italian cuisine. Reservations were made and thankfully so, because it was very crowded. We tried the spaghetti neri al pesce, which is black spaghetti with shrimp and crab in a creamy sauce. We also had the traditional lasagna. Need we say more? It’s lasagna. We washed it all down with a bottle of Cabernet.

Eating Italian is one of the best things to do in Chicago

This day was perfect for sightseeing and food. We ate our fill and were ready to sleep. Unfortunately, driving 12 hours meant we had to wake up really early the next morning to be back for that 9-5 life. And so we could pick up our dog, Luna.

Luna at home being petted

Other Things to Do in Chicago

No trip is the same. So here are 10 other awesome things to do in Chicago! Hopefully we get to do these the next time we go. Almost all of these are doable with a CityPASS or Chicago Explorer Pass so be sure to check those out!

  1. Science and Industry Museum – This museum is housed in an original building from the 1893 world’s fair and has a German submarine from WW2.
  2. Field Museum (Natural History) – Again, this museum originated from the 1893 world’s fair and is massive!
  3. Architecture River Tour – This is what we want to do most when we return. Learn more from Chicago Explorer Pass.
  4. Frank Lloyd Wright Home and Studio Tour – The famous architect’s home and studio. A must-see for art and architecture lover. Part of Chicago Explorer Pass
  5. See a show at Chicago Theater – The Wizard of Oz was playing when we visited Chicago, but leaving the country soon made our budgets a little tighter 🙁
  6. See the Chicago Symphony Orchestra – a fun thing to do in any major city, watch the orchestra perform!
  7. Catch a Cubs/White Sox game – Enjoy America’s past time by watching either the Cubs or White Sox. And have a hot dog and beer, of course!
  8. Navy Pier Rides/Games – Have a lot of fun on the pier and ride the ferris wheel! Add it to your Chicago Explorer Pass!
  9. Observation Deck Views – See amazing views of Chicago’s skyline from a skyscraper!
  10. Shoreline Lake Tour – A narrated boat tour that takes you by Chicago’s popular shoreline, making for great views of the entire city! Add this to your Chicago Explorer Pass!

Enjoy the Windy City! Happy travels!

Have you been to Chicago? What are some of your favorite things? Comment below!

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Darah and Garrett in Spain

Where Food Takes Us

We’re Darah and Garrett. Our life has been an adventure ever since we eloped in a pink Cadillac in Las Vegas. Now we’re running around the world, working online, and eating everything we can.

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5 years ago

Very cool! I only had a day in Chicago, which I wrote a blog about. But, this gives me much more to think about if I get a return visit.

5 years ago
Reply to  Ama

You should definitely go back. It’s hard to see everything in just one day…we didn’t even see everything in 3!

5 years ago

You’re right! An entire city like that must have so many places to explore and eat scrumptious food at. I’ll just have to plan an extended road trip again.

5 years ago

Love Chicago 👍🏻👍🏻

5 years ago

We do too! Writing this post really made us want to go back.