I’ve never been big on weekend travel, partly because I never thought you could see enough in only a weekend, and partly because I didn’t know where to go for a quick weekend getaway. In mid-June I spent just over 48-hours in Chicago seeing the sights of the city and trying to maxmize my short stay. Here’s how you can enjoy 48-hours in Chicago for the first-time visitor or a repeat traveler.
1. Eat Deep Dish Pizza
Deep dish pizza is a Chicago staple. Over the years that’s the one consistent thing I’ve heard people mention when they talk about Chicago – you have to try the deep dish pizza! Well, I couldn’t go all the way to Chicago and not try the pizza… partly because I just love pizza, and partly because I couldn’t miss the novelty of the experience. I went to Giordano’s to try my deep dish pizza, and they have it down to an art! Our table was beside the window looking into the kitchen where they prepare the pizzas… and I don’t even want to know how much cheese they go through in a year!
I loved it and I will definitely be back for more! If you have 48-hours in Chicago – or even less – you have to stop for a deep dish pizza.
2. Architecture Boat Tour
Chicago is famous for it’s beautiful and creative architecture. A city that prides itself on their beautiful skyline and is proud to share this with tourists and locals alike. There are numerous cruises and boat tours that offer fantastic views of the city skyline along the Chicago river. We chose the Chicago Architecture Center for our cruise and were pleased with the knowledge of our volunteer guide. The Chicago Architecture Center is a non-profit organization that offers programs, tours and exhibitions to help promote architectural innovation. The boat tour was 90 minutes and gave us beautiful views of the city from the river.
I’d highly recommend adding this to your Chicago itinerary whether you have more or less than 48-hours in Chicago.
3. Eataly
As a major city in the USA, Chicago has fantastic dining options no matter the taste or budget. Eataly Chicago was located near our hotel and offered delicious authentic Italian products. You could stop in for a full meal or just a snack – depending on your preference. There was also a few different market areas where you could purchase meat, seafood, cheese, bread, wines and other Italian staples to take home and make yourself.
We enjoyed a drink here and bought wine before heading back out to explore the city. Definitely worth a stop.
4. Navy Pier
The Navy Pier is a Chicago landmark and was on all of the lists of things to do in Chicago when I was (briefly) researching my trip. There is an indoor market, some restaurants and fast food places, rides and games and beautiful water views. It was raining off and on when we visited so I don’t think we got the “true” Navy Pier experience, but it in the short time I was there it was easy to see this was a major tourist trap. Definitely stop by if you’ve never been to Chicago before, but if you aren’t into amusement parks or fairs, it’s probably not going to take you long to get your experience and leave.
Overall, I’d say it was worth the experience, but not a full day activity.
5. Visit the Game Room at the Chicago Athletic Association
If you’re looking for some entertainment with your friends (and no kids) then head to the Game Room at the Chicago Athletic Association. There you can find food, drinks and games like pool, shuffleboard, bocce ball and cards. It’s a retro feel with big leather couches and chairs, old wood furniture, big fireplaces and dim lighting. Perfect for a date or with a group of friends. I wish I had more time to spend here and really enjoyed my fancy cocktail.
6. Mural Spotting
Before visiting Chicago I had no idea how much street art the city had. There were murals and paintings around almost every corner. If you’re looking for something to do then add mural spotting to your list. You could spend as much or as little time as you want finding these creative paintings around the city. So if you have 48-hours in Chicago you can definitely add this to your itinerary.
7. Shopping on the Magnificent Mile
You can go shopping anywhere in Chicago – but the Magnificent Mile has more than 450 shops! Pretty much anything you’re looking to buy can be found on the Magnificent Mile, and if you’re in Chicago you might need to buy some souvenirs.
8. Drinks on a Roof-Top Patio
The roof-top patio game is strong in Chicago. I’ve never heard of so many roof-top patios in one city before, but around every corner there was a patio to be found. One thing to note is that you need to plan for some extra time a there are often lines and long waits to get a prime seat on a patio. We went to London House Chicago to enjoy a drink and I think the only reason we actually made it to the top was because of the weather. Luckily for us we weren’t put off by the drizzle and hazy views and enjoyed a cocktail on the patio before getting fully rained out.
9. Visit the Bean & Millennium Park
One thing you have to do if you’re visiting Chicago is to spend some time at the Bean and Millennium Park. Fun fact: while researching Chicago I actually learned that the real name of the famous bean-shaped sculpture is “Cloud Gate” and is 110-tons of stainless steel. Head there first thing in the morning for photos without lots of tourists, or just accept that it’s a popular attraction and that you’ll have 100-ish other people in your photos. Millennium Park is a large park that offers events, exhibits and beautiful vies of the city. To get to the Bean you actually will be in the park already – so take advantage and go for a stroll.
10. Eat at Little Goat Diner
Like I mentioned, Chicago has many fantastic food options. We tried the Little Goat Diner for breakfast on our last morning and it definitely exceeded my expectations. I am still dreaming of my Elvis waffles and I want to go back and try everything on that menu. I’m sure no matter your taste you could find something to eat here, but if diners aren’t your thing you can Google the top places to eat in Chicago and find something to suit your mood. If you have 48-hours in Chicago (or more!) head to this area of the city and spend some time exploring. There is lots of street art in the area and a market as well.
11. Try Garrett’s Chicago Mix Popcorn
I love me some Chicago mix popcorn, so I had to try Garrett’s famous popcorn when I had the chance. It was the perfect blend of cheesy goodness and sweet caramel. Perhaps I stored it wrong (on my kitchen counter in the bag) but I found it didn’t keep too well. My suggestion would be to eat it within a day or two of purchasing, otherwise it gets a little mushy.
12. Visit Museums & Art Institutes
The city of Chicago had art, museums, and galleries a-plenty! If you like to visit this kind of attraction or have a love for art or architecture, then you will definitely be able to find something to do. Our architecture cruise actually came with entrance to the Architecture museum so that’s a way to save money and experience the city. We didn’t actually use this option because we didn’t have enough time, so if you have more than 48-hours in Chicago you will have plenty of time to experience the city.
13. Eat at Portillo’s Hotdogs
Before visiting Chicago I had never heard of Portillo’s Hotdogs, but apparently it is a Chicago landmark. We went for dinner here and I got the famous beef sandwich… it was delicious! There was so much meat, and I didn’t even need a side. I did however have to get the chocolate cake to go with it, because apparently it has a fantastic reputation. I will say that the cake was a little bit of a let-down. So if you visit, try the cake and let me know what you think!
Other Activities
There are so many other activities and attractions that you could add to your itinerary for 48-hours in Chicago. Depending on your interests you can visit the Shedd Aquarium, have your pick to watch numerous sports teams, visit the Skydeck or Willis Tower for city views, or head to the Lincoln Park Zoo. Options are pretty extensive to spend your weekend… you might even need longer than 48-hours in Chicago.
48-Hours in Chicago Summary
Well, it can be done! An itinerary with 48-hours in Chicago may seem too short, but there is a lot you can fit into a weekend getaway. If you want to extend your stay you will definitely have enough options to fill your days and you probably still won’t see all of the sights. I definitely enjoyed my 48-hours in Chicago but am already planning on what I want to see on my next trip.
What are your favourite things to do and see in Chicago? If you’re looking for help planning an itinerary, check out some of my other posts for itinerary planning!
