How to Spend 2 – 3 Days in Chicago

Chicago has been on my bucket list for the longest time. I’m an architecture geek, and a lover of blues music, so it’s naturally a good fit. Chicago really did exceed my expectations; the dynamic architecture, the street art, and the general vibe of the place were all incredible. Here’s my guide on how to spend 2-3 days in Chicago, including some tips to handle Chicago on a budget. I’ll give you some suggestions for what to do in Chicago in 2 days; and then list extra activities for if you are lucky enough to have 3 days in this lively city.

Check out my other articles from our #HendersonsWildWest trip – Visiting Carhenge in Nebraska, and our 4-day tour of Yellowstone!
More coming soon!

Where to stay in Chicago

We stayed at the Best Western Grant Park, and found it to be a great combination of mid-range budget and convenient location. The Best Western is only 1 mile from ‘The Bean’; and near many south of the river attractions and restaurants, but cheaper than staying on the Magnificent Mile. If you’re looking for a bit of luxury, with prime river and lake views, try The Langham – right near the the Wrigley Building. For a budget option, try the HI Chicago Hostel, right near Grant Park. Transport networks in Chicago are really good, so there are plenty of hotel options outside the centre too.

Transport

Getting to downtown Chicago from O’Hare airport is very simple. The Blue Line train goes all the way from O’Hare to downtown, and takes around 55 minutes. Tickets cost double coming in from the airport than when you return. But as of September 2019, that was still only $6 instead of the usual cash fare of $3. From various downtown Blue Line stops, you can connect to the other metro services. Single train tickets last for 2 hours and can include connections.

Things to do in Chicago in 2 days:

Cloud Gate ‘The Bean’

Notably one of Chicago’s most visited and recognisable sites, ‘Cloud Gate’ by artist Anish Kapoor is a photographer’s dream. Affectionately known as ‘The Bean’, the organic and sinuous lines of Cloud Gate are endlessly interesting. The reflective surfaces mirror the Chicago skylines and create undulating versions of its surroundings. I fell in love and went back a number of times on our visit.

Grant Park

Grant Park is home to many interesting sculptures. If you are staying in any of the hotels along this end of Michigan Avenue, it’s a pleasant route to walk if you are heading downtown. At the south end, is the fascinating modern sculpture ‘Agora’ by artist Magdalena Abakanowicz. Near the E 9th Street entrance, the John Alexander Logan monument sits elevated on a grassy knoll. Further north, near the Van Buren train station, there is the Seated Lincoln statue. Don’t miss ‘Crown Fountain’ either, by Catalan artist Jaume Plensa and built by Krueck and Sexton Architects.

Budget tip: None of the above sights require entry fees. There is so much to see in Chicago for free!

The Art Institute of Chicago

The famous Art Institute of Chicago can get very busy, so I would recommend buying a fast pass ticket; or buy a GO Chicago activity pass. One of the oldest art institutions in North America, it is known for its progressive curatorial spirit, that appeals to a broad range of visitors.

See more of my street photography and art here

Architecture River Boat Tour

An architecture river boat tour was on my absolute hit-list of things to do in Chicago. The diversity of architecture in Chicago is legendary, so a river cruise to admire it all (and learn so much more), was a must! We chose the Tours & Boats river cruise which leaves from River City Marina, as this was convenient to our hotel. The information we gleaned about both the city and the architecture along the river was so illuminating – I cannot recommend this activity more highly. If you’re on a budget, look out for Groupon or discount deals. Here are just a selection of the photos:

360 Chicago Observation Deck

I’ll be honest, this wasn’t at the top of our list of things to do, because my husband is afraid of heights. But a friend gave me a free ticket, and my husband volunteered to stay in the café at the bottom! My visit to the 360 Chicago Observation Deck turned out to be one of my favourite activities in Chicago. From a tourist’s point of view, it is a great way to orientate yourself in the city and get a bird’s eye view of some famous landmarks. As a photographer, it allowed me to get a different perspective on the incredible architecture of Chicago.

Magnificent Mile

This affluent stretch of Michigan Avenue is full of luxury shops, high-end apartments and historic landmarks. I highly recommend starting your visit up at the 360 Chicago lookout, and then making your way back down to the river, enjoying the landmarks along the way. The beautiful Chicago Water Tower, which was the only public building in the burn zone to survive the 1871 Great Chicago Fire. The gothic revival Fourth Presbyterian Church and parish house is a calm sanctuary amongst the high-rises and buzzing shops along the Mile. Closer to the river, be sure to admire the legendary Tribune Tower and Wrigley Building. Budget bonus – wandering is free!

3 days in Chicago

If you have a third day in Chicago, I recommend some of the following activities:

• Take a day trip to Frank Lloyd Wright’s Oak Park
• Go on a boat tour of Lake Michigan
• Take a walking tour, or if you’re on a budget, why not do the river walk yourself?
• On a budget? Enjoy a picnic on one of Chicago’s many beaches!
• Visit Navy Pier – a great activity for the family

Fun Fact: Did you know that Chicago’s waterfront along Lake Michigan is protected from development? Meaning there are lots of nature walks and beaches along the shore!

Where to eat in 3 days in Chicago

So, I asked the fine folks on Twitter this question and it became hot debate. Deep dish pizza preferences were bandied about, and gauntlets were thrown! In the end, here is where we ate, and we enjoyed it all:

Gino’s East + Comedy Club

• (500 N LaSalle Dr) – Gino’s people saw our banter on twitter and offered us tickets to their comedy club. We decided this was a perfect first night activity after our big day of travel from France. The comedy show was really hilarious, and our deep dish pizza was huge and tasty. I recommend you just get a small deep dish pizza to share between two, as they are so filling! [Disclaimer: The tickets to the comedy club were gifted to us, however we paid for our drinks and pizza – and as always, all opinions are my own]

Avec

• (615 W Randolph St, West Loop) – We met up with a friend at Avec and couldn’t have been happier with her choice. The chorizo stuffed prunes wrapped in bacon were to die for. Seriously, do yourself a favour and eat here.

Lou Malnati’s

• (805 S State St, South Loop) – We had been advised to try the butter crust deep dish at Lou’s and it didn’t disappoint. We received a coupon from our hotel for a free cookie dessert with our purchase, so the bargain-hunter in us couldn’t resist. I enjoyed the crust more on this deep-dish, but found the flavour of Gino’s sauce more enjoyable. It’s a tough gig, this pizza testing!

Dollop Café

• (801 S Financial Pl) – This bright and airy cafe is a great pitstop if you’re in the South Loop. It actually appealed to us as a place to work (free wifi), because of its minimalist aesthetic and sweet sweet mochas!

Buddy Guy’s Legends

• (700 S Wabash Ave) – Much like Gino’s, this is a great combo activity – food and entertainment. We knew we’d get a wonderful and skilled show, but what we weren’t expecting was Buddy Guy himself taking to the stage and giving us a fabulous rendition of ‘Hoochie Coochie Man’. Buddy was a real gentleman too, signing a souvenir for my husband. Food-wise, it is southern and creole standards and traditional bar snacks.

How to spend 2 – 3 Days in Chicago

I could easily have spent a week or more in Chicago, to include trips to Frank Lloyd Wright’s Oak Park and time to walk more of the River Walk. And I’m sure after your 2 – 3 days in Chicago you will agree, and vow to return, as I have done. Chicago is one of those cities that I just knew I’d love, and it surpassed my expectations by a mile. There was an energy in this city that captivated me – busy but not frenetic, gritty but in a good way, and lively without being exhausting. Spending 3 days in Chicago was everything I hoped it would be.

Planning a trip? Take some of my planning advice. Love my photos? Check out my portfolio on Shutterstock!

All photos & content © Hannah Henderson and may not be used without permission (sharing this blog post is fine, though!). Images shot with a Canon DSLR T3i Rebel + Canon EF-S 18-135mm f/3.5-5.6 IS STM; and an iPhoneX.