2 Days in Chicago at Krista Aoki, a lifestyle & travel blog | things to do in Chicago, CityPASS, traveling, skydeck, big bus, tour

Chicago in 2 Days

February 8, 2017
2 Days in Chicago at Krista Aoki, a lifestyle & travel blog | things to do in Chicago, CityPASS, traveling, skydeck, big bus, tour

How do you get the most from Chicago, as a traveler, in two days? Unfortunately my first time in Chicago was very limited as I could only spend two days there. Chicago is an icon of American history and its community is diverse. I wanted to make sure that I got the most out of my short experience.

There will be so much to see and experience while you’re there. The Windy City is home to so many attractions, museums, restaurants, and shopping! How can you fit it all into just two or three days?

This guide is for you travelers who:

  • Would like to make the most out of their short stay in Chicago
  • Want to learn about Chicago’s history and culture
  • Would enjoy seeing Chicago’s popular attractions

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Getting Around

I hate driving around cities I’m unfamiliar with. The intersections could be weird, if you miss a turn it could be a complicated way around, what if there are confusing one-way roads, and it could just be an all-around frustrating experience. Plus, I don’t want to worry about the added cost of paying for parking.

Here’s how you can get around carless in Chicago:

  • Chicago Transit Authority: Chicago’s public transit operates via buses and railways. You can buy a one-day, three-day, or seven-day pass to really make use of public transportation during your stay! You can even download apps to make traveling from point A to point B so much easier. 
  • Lyft: I love using Lyft whenever I visit cities. First of all, Lyft designed their smartphone app to be easy to use. Plus, calling a Lyft is cheaper than calling a taxi! Whenever you’re ready for a ride, open the app on your phone. You can easily enter your current location, and the destination. From there, the app tells you the estimated cost of the trip as well as how long it may take for a driver to reach you. If you use my link to sign up for Lyft, you get $15 towards your first rides!


2 Days in Chicago at Krista Aoki, a lifestyle & travel blog | things to do in Chicago, CityPASS, traveling, skydeck, big bus, tour

I felt fortunate to stay at the Gwen hotel along downtown Chicago’s Magnificent Mile (known for its shopping, restaurants, and hotels). This luxury hotel is typically expensive, but we stayed there during Chicago’s off season for the best rates. (for more amazing travel tips, click here!)

Accommodation preferences are different for every traveler! Here are websites I recommend for you to start your research:

  • TripAdvisor: What I love about TripAdvisor for hotel research is it is a central location to look at hotels in the city with oftentimes detailed reviews of the hotels. They also have a feature where you can look at the rates for the hotels through various sites. So they basically do your research for you to get the lowest rates!
  • AirBnB: AirBnB is a great alternative to a hotel. You can search for anything from a room in someone’s home or apartment, to a private apartment or home. AirBnB offers a unique experience for travelers! I love seeing the different ways people decorate their rentals. If you use my link to sign up for AirBnB, you get $35 in travel credit towards your next stay!
  • Hostels: Mike’s favorite part about staying in hostels is hearing the ins and outs of the town. He’s learned so much about the surrounding area from others at the hostel where he’s staying! You can even compare hostel prices using Tripadvisor (just search for “Hostels” in Chicago). 

Enjoy a Chicago Deep Dish Pizza

Chicago is known for its delicious deep dish pizzas, so you have to make room for this dish during your stay here.

Eat a deep dish pizza at one of Giordano’s 18 Chicago locations. Their double-crusted, cheese stuffed pizza makes national headlines and you deserve only the best.

Hop On & Hop Off! Chicago Style

2 Days in Chicago at Krista Aoki, a lifestyle & travel blog | things to do in Chicago, CityPASS, traveling, skydeck, big bus, tour

I’m sooo happy I decided to get a Big Bus pass when I visited Chicago. With your Big Bus pass, you can hop onto their two-decker bus at any one of their 14 stops scattered throughout the city, and hop off within walking distance to landmarks including:

  • Adler Planetarium – did the movie La La Land completely and totally romanticize planetariums for anyone else!? 
  • Art Institute of Chicago
  • John Hancock Center & 360 Chicago
  • Magnificent Mile – famous for its amazing selection when it comes to shopping, restaurants, and hotels!
  • Michigan Avenue Bridge
  • Millennium Park – the largest rooftop garden where the “bean” is!
  • Navy Pier
  • Shedd Aquarium
  • Soldier Field
  • The Field Museum
  • Willis Tower & Skydeck – for the daring ones courageous enough to step onto a glass box above the city!

Once you hop on, you’re taken on a guided tour throughout Chicago to see its attractions and landmarks. The entire circle (without hopping off) is about two hours long! So you get an insane amount of coverage and the added opportunity to stop at 14 of Chicago’s popular attractions and locales.

Plus, having a Big Bus pass eliminates:

  • worrying about driving through traffic;
  • struggling to find a parking spot in the city; and,
  • paying for parking!

You can buy a one-day, two-day, or three-day pass! So it is perfect for travelers visiting Chicago for a couple days, and travelers who want to see Chicago’s attractions during their stay. If you’re trying to see as many of Chicago’s amazing attractions as you can, get a Big Bus pass! Use the code “BBT10CHI” to get 10% off 2-day and 3-day Big Bus pass tickets!

Take Advantage of CityPASS

2 Days in Chicago at Krista Aoki, a lifestyle & travel blog | things to do in Chicago, CityPASS, traveling, skydeck, big bus, tour

Does anyone else freaking love CityPASS? I love getting to see each city’s attractions! You learn about their history and get a peek into the culture. Plus, these attractions make for great photo opportunities (hellooo, Instagram)! Use CityPASS to see multiple attractions at a discounted price.

Plus, with a Chicago CityPASS you get to freaking skip the line!! If you have limited time in the city, this is essential to get the most out of your experience!

Your Chicago CityPASS gets you VIP and express entry into:

  • Shedd Aquarium
  • Skydeck Chicago
  • Field Museum
  • Museum of Science and Industry or 360 Chicago
  • Adler Planetarium or Art Institute of Chicago

(Their prices are changing on March 1! If you are visiting Chicago within the next six months and you want to travel with CityPASS, use this link to book your CityPASS now. You can redeem your booklets within six months of purchase.)

Protip: You can combine your CityPASS with the Big Bus Tour. The Big Bus Stops at all of these CityPASS locations except the Museum of Science and Industry.

Go on a River Tour

2 Days in Chicago at Krista Aoki, a lifestyle & travel blog | things to do in Chicago, CityPASS, traveling, skydeck, big bus, tour

History and architecture buffs will love going on a guided river tour. If you’ve never been to Chicago before, you have to add this to your list.

  • See the way the city itself is built on multiple levels from a boat on the Chicago river;
  • Learn about the innovative architecture designed by architects who made history books;
  • Learn about the very interesting history of this city, including where and how they rebuilt Chicago after the Great Chicago Fire of 1871.

I recommend the First Lady Cruise’s Chicago Architecture Tour. The tour guide I had was funny, personable, and knowledgable. Pretty much everything you could ask for in a guide! They pack so much information into a 45 minute Chicago river tour.

If you’re taking the Big Bus, stop at Fort Dearborn and the First Lady River Cruise is a short walk around the corner!

Take Pictures & Have Fun!

2 Days in Chicago at Krista Aoki, a lifestyle & travel blog | things to do in Chicago, CityPASS, traveling, skydeck, big bus, tour

While you’re in Chicago, there will be so much to see. Explore TripAdvisor for inspiration when you are planning other fun activities in the area! 

Don’t forget to take plenty of photos during your short time there. Want to turn your digital photos into prints? Download the Parabo smartphone app (iTunes)(Android) and use my code KRISTA. With my code, you can turn your beautiful vacation photos into 25 physical square prints for free! All you have to pay for is shipping. (P.S. Want to edit your vacation photos to look beautiful for social media? Check out my guide on how to use VSCO to create beautiful images!)

All in all, I absolutely loved exploring Chicago, and can’t wait to go back to experience more. What are your recommendations for activities to do and food to try in Chicago?! I know that I only experienced a small part of what this city has to offer, so I will have to add your recommendations to my itinerary!

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  • Frederick

    Wow sounds like a heck of a time! River tour would be so nice to check out all the amazing architecture. I’d recommend being there for st paddys day for when they turn the river green! It’s super cool!

    • What! They turn the river green?! Now I have to visit this city during one of these St. Patrick’s days!

  • Chicago looks wonderful! I will go their just to that Chicago deep dish pizza!

    • Oh my gosh, yesss! Be prepared to gain a little bit of weight on your trip haha to be honest I wasn’t.

  • It’s so weird I have never been to Chicago as my boyfriend is from there and my best friend went to UChicago! Now I guess after this post I’ll have to go!


    • Yay, Claudia it sounds like you’re destined to go. 🙂 Let me know what you end up doing! Maybe your boyfriend and best friend have the insider info on the best things to do while you’re there.

  • How fun! I was there for a conference a couple of years ago, but didn’t get time to see anything! I can’t wait to go back and explore Chicago more!! Thanks for the tips!

    • Traveling for conferences can be super awesome except being unable to actually see the city. I hope you get the opportunity to see a little bit more next time!

  • This is so informative. One day I will visit Chicago 😉

    • Thanks Shoshana! Let me know what sights you catch once you do. It was the first city I visited in the Midwest.

  • I’ve always wanted to visit Chicago! This is great information and has definitely peaked my interest to go sooner rather than later!

    • Yay! I didn’t consider Chicago as a destination initially. I actually visited because one of my favorite bands was touring there. But I’m so glad I ended up being able to explore everything!!

  • Vy

    We LOVED Chicago, and I LOOOOOOVE CityPASS. I feel like we got a lot in common, Krista!

    • Oh my gosh yesss Vy! CityPASS is my go-to when I visit a big city!

  • I used to live in Chicago, and the one thing I learned is that it truly is the windy city! There was no point in doing my hair because the minute I walked out it was all over my head lol

    • haha! My coworkers were telling me that it gets sooo windy and cold there in the winter! Dang I have long hair too, I hate when that wind catches all over my face! Thanks for the heads up Ashleigh, I’ll remember that next time I go.

  • Chicago looks so fun! I would love to go on one of those river tours. Definitely getting one of those CityPasses when I go!

  • Chicago is one of my favorite cities to visit. You can do a quick weekend or spend several days there and not run out of activities! I have to disagree on your pizza recommendation, though…I’m a Gino’s East girl! Haha 🙂

  • Chicago looks wonderful, great review! Thanks for your suggestions very informative post i love to visit Chicago one day !!

  • Chanelle Lynn

    Awww, it looks like you had so much fun!! I would love to visit Chicago!


  • I am so glad that you wrote this post. I want to do Chicago for my birthday and it will definitely be a weekend trip. This helped alot.

  • I also enjoyed Chicago a lot but I only had a few hours!!! Such a beautiful city! I shared 3 experiences in my blog which I hope you can check out as well 🙂