3 Day Chicago Itinerary
3 Day Chicago Itinerary

Ultimate 3 Day Chicago Itinerary – Maharaj’s Recommendation

I always wanted to travel to a foreign country but never thought that my first country would be the USA. I also thought I’d travel because of my blog, but well, it was my work that took me on my first international trip.  As part of attending KubeCon in Chicago, I spent a week in Chicago and trust me those were some of the best moments of my traveling experiences. 

Further, this was also the first time I flew the Emirates A380 which was another bucket list item that I ticked off my bucket list. So a lot of first on this trip. Though I was busy with the conference, I did take time off to explore the beautiful windy city. In this post, I’m going to share a 3 Day Chicago Itinerary based on my experience. 

So save this blog post for your next trip to Chicago and let’s get started.

Arriving in Chicago

O’Hare International Airport is the airport that serves the city of Chicago. It’s one of the largest airports in the world and has direct flights from many destinations including the likes of India, the Middle East, Australia and over 200 other places. The massive airport has 5 terminals with 214 gates and 8 runways making it one of the largest airports in the world. Most international flights arrive and depart from Terminal 5. 

O'Hare Airport Metro Station
O’Hare Airport Metro Station

There’s an airport transit system in place which connects all the terminals to the O’Hare Metro station which further connects you to the main city. There are cab services available at the airport, however, if you have time, relatively less luggage and want something affordable, take the Chicago Metro to the city. For under $10, you can travel from the airport to the city. Read my Chicago Metro Guide to know more everything about the Chicago Metro.

Chicago Metro Ventra Card
Chicago Metro Ventra Card

Hotels in Chicago

When it comes to hotels in Chicago, the city caters to every traveller’s preferences and budget. For the budget-conscious adventurer, there are a few hostels in downtown that offer an affordable and communal atmosphere, perfect for making connections with fellow travellers.

If you’re seeking a more conventional stay with added comfort, I’d suggest booking a hotel in downtown Chicago, including “The Loop,” Millennium Park, and Millennium Mile. All these areas boast a variety of hotels catering to all your needs.

I stayed at different places during my stay in Chicago. I stayed at the Hi Chicago Hostel for a few days, relishing the lively ambience and central location. Later, a stay at the Palmer House Hilton Hotel allowed me to indulge in the epitome of luxury. PS: This was offered by the conference organizers. I’ll be talking about both of these places in the upcoming blog posts.

3 Day Chicago Itinerary
3 Day Chicago Itinerary

3 Day Chicago Itinerary

Day 1 –  Field Museum, Shedd Aquarium & Adler Planetarium

On your first day, you can start a little late and visit the Chicago Field Museum. You can either take a cab and go or take the metro like I did. The nearest station is Roosevelt. It’s a considerable walk from here to the museum, but it’s a wonderful walk through the park. Pass through the Agora art installation which comprises 106 headless and armless iron sculptures.

Make your way through Grant Park and visit the Field Museum. You surely need a good 4-5 hours to cover everything in the museum. I regret not having that time, but I’m glad that I could visit the museum. If you’re a history buff, you cannot miss out on this. If you’re with kids they have a nice dinosaur and animal kingdom area. 

Inside Ancient Egypt
Inside Ancient Egypt

After your visit, you can visit the Shedd Museum and Adler Planetarium which are on the same campus. Both these places are perfect for kids as well as adults. I couldn’t visit those because of the time constraints. By the time you complete this, you’ll be closing in on your day. Post that you can have your dinner at Giordano’s and relish a Chicago-style deep dish, but with an Italian Touch.

Super Veggie Deep Dish Pizza At Giordano's
Super Veggie Deep Dish Pizza At Giordano’s

Day 2 – SkyDeck Chicago, Millennium Park, Chicago Bean

On day 2 you can start your day by visiting the tallest building in Chicago – Skydeck Chicago. It’s an observatory located on the 103rd floor and it opened to the public in 1974! The views are stunning and offer a beautiful view of the city. I’d suggest going in the morning to avoid the rush. Also, take the general ticket, the whole walk from the entrance to the elevator is quite interesting.

Edge Skydeck Chicago
Edge Skydeck Chicago

After completing this activity, you can have a quick breakfast on the ground floor of Skydeck Chicago. It’s a food court and there are multiple options to eat. Or you can visit places like Corner House Bakery, Starbucks, Dunkin Doughnuts and other similar places. 

After breakfast, you can visit Millennium Park. There’s no entry fee here so you can just walk in. It’s a massive park so beware that you’ll have to walk a bit. See the Wrigley Square, Jay Pritzker Pavilion and the famous Chicago Bean. If you’re visiting around Christmas make sure to check out the Chicago Christmas tree in the park. Also note that, when I visited the Chicago Bean was closed, so I couldn’t go near it.

Chicago Bean, Millennium Park
Chicago Bean, Millennium Park

From there walk towards East Monroe Street and check out the Chicago Stock Exchange Arch. This arch is the only surviving part of the Chicago Exchange that was bustling in the 1800s. Next to it is the Art Institute of Chicago which is again a must-visit for anyone who loves art and architecture. Based on your time you can visit this or skip. 

Walk towards the Abraham Lincoln statue before arriving at Buckingham Fountain which was developed in the 1920s. During winter the fountain is turned off due to the weather, so I didn’t get to see it operational. From here cross the road and visit Queen’s landing. Witness the massive Lake Michigan appreciate the Chicago skyline and spend your evening in the park. 

Tip: The best part about this 3 day Chicago itinerary is that you can swap days/activities based on your liking.

Day 3 – Magnificent Mile, Navy Pier & Chicago River Cruise

The third day can start with breakfast at the Goddess & The Baker. It’s a wonderful cafe located in the loop and quite a popular one among the locals. If you’re a vegetarian, this serves Vegan food as well. You can read more about Vegetarian restaurants in Chicago to know more. 

After breakfast, you can start walking toward Magnificent Mile or Mag Mile as it’s called. While you can take a cab, I’d strongly suggest walking. There are numerous buildings in the vicinity that you must see, some of them of historical importance as well. Walk past the DuSable bridge to cross the river and reach the Chicago Tribune building and just gaze at the beautiful amalgamation of historic and modern buildings, trust me you’ll love it!

From here, you can go walking on the Magnificent Mile which has a lot of luxury shops. So it’s a good place to shop. But mind you, it is expensive. You can also visit the World’s Largest Starbucks In the World and grab yourself a coffee or a snack.

Visiting World's Largest Starbucks Reserve Roastery in Chicago
Visiting the World’s Largest Starbucks Reserve Roastery in Chicago

Post this you can either take a cab or if you have the stamina, take a walk towards the Navy Pier. It’s one of the places that you must visit. A good place for kids with lots of food and activity. From here, you can walk down the river walk and get ready for your river cruise – a must for any Chicago itinerary.

Talking about river cruises, there are two of them. One is an architectural tour while the other one is just a regular around Michigan Lake. I’d strongly suggest taking the Chicago River Cruise which involves the architectural tour. The tour starts from Michigan Avenue (near the Apple Store). You can buy the tickets online, or from the ticket counter there. 

Shoreline Cruise in Chicago
Shoreline Cruise in Chicago

The Chicago River tour is an activity that you must do when in Chicago. It’s a 60-minute guided tour and it’s worth it. The story of the windy city and interesting facts along with the aesthetically pleasing buildings is just beautiful. You can take the cruise at any time of the day, but I’m sure it looks more beautiful during the evening. 

After your boat trip, you can take a stroll in the river walk and then take an exit toward the Grand metro station for dinner. From here head to Pizzeria Uno, which is home to the original Chicago Deep Dish Pizza. Mind you this place has waiting so make sure you calculate that before visiting. If not here, you can also dine at Lou Malnati’s for a Chicago Deep Dish Pizza which is close by. 

Spinoccoli - deep dish pizza.
Spinoccoli – deep dish pizza.

Once you’re done with your 3 day exploration of Chicago, take a stroll back to your hotel appreciating the time you spent in the windy city. And tell me genuinely, isn’t Chicago beautiful? I thoroughly enjoyed my stay in Chicago and if I ever get time to revisit Chicago, I’ll surely spend more at these places and even explore more. 

If you’re extremely short on time, then you must include the following places in your Chicago itinerary:

  • Take The Chicago River Cruise
  • Visit Millennium Park & Chicago Bean
  • Experience Skydeck Chicago
  • Eat Chicago Style Deep Dish Pizza

When Are You Visiting Chicago?

My first international trip to Chicago was an absolute delight, and I couldn’t have asked for a better experience. I genuinely loved strolling through the city, taking in its vibrant atmosphere and discovering beautiful buildings along the way.

If you’re planning a trip to Chicago, I hope this 3 day Chicago itinerary will help you plan your trip. Feel free to share this itinerary with friends and family, and if you have any additional recommendations or places I might have missed, drop them in the comments below. Tweet to me at @Atulmaharaj, DM on Instagram or Get In Touch. I can also help you with a personalized itinerary for Chicago.

Happy exploring!

About Atulmaharaj

A seasoned blogger and a content marketer for close to a decade now. I write about Food, Technology, Lifestyle, Travel, and Finance related posts. Blogging brings me joy and the best part is I get to read and e-meet so many amazing bloggers! PS: I'm also the founder for Socialmaharaj.com :) Favorite Quote: "Traveling is like reading a book, one who hasn't traveled, hasn't turned a page.

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