How to spend a weekend in Chicago

We love to travel, but we have full-time jobs, so we can only visit certain places on weekend trips. Chicago is one of those cities that was up there on our list. Here’s how we managed to spend a weekend in Chicago on a budget. 

This post is part of our weekend trip ideas. Here are other places we visited that may inspire you to visit on a weekend too: 

• Weekend in Gainesville Florida with a toddler
• Daytona Beach Weekend Getaway (with a toddler)
• How to Travel Every Weekend
• Treat Your Weekend as a Vacation
• Weekend at Holiday Inn Club Vacations Orange Lake

Arriving in Chicago, we had no idea what we wanted to do. We just thought we would wing it without researching too much but narrowed it down to a few must-sees: the Bean, going up the viewing area of Willis Tower and walking down the Magnificent Mile. A lot of those are free, but we wanted to make the most of the weekend, and we somehow ended up at a Tourist Information Area to ask more about Chicago Tourist attractions. 

If you want a more informal narrative about our Chicago trip, you can check out Peter’s other post called A Journey to Chicago. 

Chicago’s Greatest Hits – How we spent a weekend in Chicago

With too many places to see with too little time, here’s what we did over the weekend, which captures Chicago’s Greatest Hits. We’ll include more things to do on a weekend after the summary post below. 

Day One of your weekend in Chicago:

• Wake up early and go downtown to see the Bean sculpture and walk around Lurie Garden and Maggie Daley Park. The parks are huge, you can also take your time looking at the sculptures around the area. 
• Head straight to Willis (Sears) Tower as soon as they open to get up to the Skydeck.
• Walk around the downtown area and gaze at all the high-rise buildings 
• Have a Chicago deep-dish pizza at Giordano’s across the street from the Willis Tower for lunch
• Take a boat tour of the Chicago River to learn more about the canals and locks that made the river a lifeline of the city 
• If you are feeling up for it and still have time, head to the Navy Pier to take an architecture boat tour or just enjoy the entertainment on offer. 
• Have dinner and head back to your hotel OR walk down the Magnificent Mile at night before heading in 

Day Two of your weekend in Chicago: 

• Have a day to spend in a museum (or two) of your choice. We would recommend the Shedd Aquarium of the Field Museum if you have time. If you’re an art lover, the Art Institute of Chicago is a must-see, and then, of course, the Museum of Science and Industry.
• Fly home in the evening

If day one in the itinerary is a bit more packed than day two, feel free to split them into two different days. When we went to Chicago, it was pre-baby, and we were game to do multiple things on the same day to free up time to go to the museums the next day. How long you spend in the museums is up to you, but my husband and I love them since they’re a great source of learning, and can spend a whole day in one of them.  

When traveling with a young child (a baby or a toddler), depending on your child’s interests, don’t expect to wake up first thing and try to hit all the ‘must-sees’ within a day. If we went to Chicago and brought our boy, we would probably need to spend time in a children’s museum or playground that he sees along the way! 

Where to Stay in Chicago

There are plenty of hotels to stay in while in Chicago, and here are some ideas. Best of all, the hotels we’ve mentioned are bookable by points! So you can definitely have a really cheap weekend in Chicago while utilizing points and miles. 

Holiday Inn Elk Grove Village

We personally stayed at the Holiday Inn in Elk Grove Village since the conference I was attending was being hosted there. It is not remotely close to the downtown Chicago area where most of the tourist spots are, but it is relatively close to Chicago O’Hare’s airport. There is a shuttle that takes you from the airport to the hotel and back but you will need to pay a small fee for the convenience. 

Kimpton Hotel Monaco Chicago

We love Kimpton hotels so much that we figured we’ll include the Kimpton Hotel Monaco Chicago on the list. Only a mile’s walk from the Willis Tower and less than a mile to the Chicago Bean, this hotel is centrally located in the downtown area. What we love about Kimpton hotels are their amazing bathroom amenities. Their scent is distinct and we love using them! The service at the Kimpton Hotel is also great, and you can redeem IHG points to stay at Kimpton hotels for almost free!

Hyatt Regency Chicago

Another hotel brand we love and keep coming back to is the Hyatt. There is a Hyatt Regency fairly close to the Kimpton and also within the downtown area. It makes it so much easier to get around the tourist sites since there are multiple metro stations to hop on around in the Loop area. The Hyatt Regency Chicago is steps from the river, so some locations in the hotel provide awesome views, and best of all, the hotel can be booked using points! 

What to do for a weekend in Chicago 

Take a boat tour of the Chicago River

It’s nice to relax and take a guided boat tour through the Chicago River. This is the same river that gets dyed green during St Patrick’s Day festivities every March. Your boat will go under bridges and your guide will point out buildings of interest as well as provide a brief background. Think of it as a history tour without being boring. 

We like taking boat tours since it gives us a different perspective than just walking around on land. Plus it’s also nice to look up at all these luxury condos and buildings by the water to see how the other half live! 

Visit the Skydeck in the Willis (Sears) Tower 

Bucket list moment! The Skydeck is a great place to go and conquer your fear of heights. The best part is the all-glass viewing deck where you can get a photo to commemorate your trip up there. The best time to go is first thing in the morning when they open. You can be one of the first on the viewing deck and don’t have to queue a long time to get the photo taken. You’ll get to beat the crowd too, but when arriving on a weekday, it can be a bit tough commuting during rush hour. 

Take a photo by the Bean Sculpture 

Another bucket list thing to do is to take a photo in front of The Bean sculpture (officially known as Cloud Gate). It is free to enter and is open from 6 am to 11 pm. Take as many photos from different angles as you wish. The parks by the Bean sculpture are massive as well, with other sculptures and flower gardens with walking trails. You can spend hours just trying to walk around that area. It is fairly close enough to the downtown area and is only a mile to Willis Tower. 

Learn more by visiting one of the museums Chicago has to offer 

Museums are great, they teach you so much about the history and all the priceless items that are within their collection. Some museums are so huge with thousands of items on display that you’ll need to spend hours just looking at all of them. Luckily, Chicago has a lot of museums to choose from. 

There’s the Field Museum, which focuses on natural history, and the Shedd Aquarium, which has aquatic animals in a huge setting. Love art? There’s the Art Institute of Chicago. Want more hands-on exhibits that focus on STEM topics for your child? Then the Museum of Science and Industry is a must-see. These are just the biggest museums in the area, there’s a children’s museum also in the area, plus other ones I haven’t mentioned since I didn’t get a chance to visit them yet. 

Plenty to see and do, and you definitely would be spoiled for choice when it comes to things to do on a weekend in Chicago.  

Go to the Navy Pier 

Want to ride a Ferris wheel in Chicago? Head on over to the Navy Pier. It’s partly an amusement park, part arcade, part convention center, and also the dock for lake boat tours. Bring your children here for hours of 

Is it worth it to do a lake tour when I’ve already done a river tour in Chicago? 

Yes! First off, the point of view is different from both experiences. The river tour is also on a smaller boat, and you’ll only see a small side of downtown. The biggest draw for me on the river tour is the history and going under a lot of the bridges that people pass through. 

With the lake tour, you can opt to do a sunset tour where you’ll see the sunset over the famous Chicago skyline. There’s less history and narration and more of a chill-out vibe as you soak in the sights. Best of all, for those who get seasick, there’s very little chance that you’ll get seasick on any of these tours. 

There are some small shops that you can browse around in and get souvenirs from. Overall, the Navy Pier is a good activity to do after dark, when most of the downtown sights are closed for the day. 

Eat a Chicago Deep Dish Pizza 

We can’t go all the way to Chicago without having one of their famous deep-dish pizzas, right? We headed off to Giordano’s in front of the Willis Tower to try one of their specialties. Giordano’s is a chain that was originally founded in Illinois. While they have 2 locations in Orlando, we still went to get the OG in Chicago. If you asked me, my favorite will be the meat and more meat pizza, but that’s totally up to you what you want to get! 

Warning: These pizzas are so huge they’ll fill you up very quickly and you may only need just the one slice to get you through the afternoon.  

A Weekend in Chicago 

There are still so many places to visit in the Chicago area and one weekend is definitely not enough. Luckily, Chicago is a big city where airline service can be fairly regular so you can opt to come back over and over again. I will probably make more than one trip back to Chicago since there is a seminar/conference I plan to attend often! 

Will update the post with more ideas once I go back to Chicago, and until then, happy weekend travels! Let me know if you have any ideas on where else I should go that haven’t been covered in the comments below.