Best Things To Do In Chicago

Are you heading to Chicago for a weekend trip!? Here are all the best things to do in Chicago if you’re only there for a few days!

If you’re going to Chicago for the first time, I totally understand how overwhelming it can feel. The parking situation, finding an affordable hotel, the endless things to do and see… it can be a lot. Especially, when you want to do as much as possible in just one weekend!

I’m here to help! This is exactly how I felt when my boyfriend and I took a weekend trip to Chicago for our anniversary. We wanted to pack in as many activities as possible in our weekend stay, but still have time to relax, walk around and enjoy the city.

Below I’ll share our favorite restaurants to eat at, attractions to see, activities to do and a few tips we learned for stress-free parking for your first time in Chicago.

Keep reading for our list of the best things to do in Chicago in one weekend!

Where to Park in Chicago

The parking situation in Chicago is not ideal, even if you’re staying at a hotel. Parking is always extra and if you don’t plan ahead, it can be really stressful and expensive. However, we discovered the Spot Hero app, which made finding and booking a parking spot for the entire weekend a breeze.

We were able to book parking in downtown Chicago for $30 from 8am on a Saturday to 8pm Sunday night. The Spot Hero app is a game changer! It’s so simple and easy to use. Once downloaded, simply search for the city or location where you’d like to park, enter the time frame you need parking for, and the app will populate a map of all the parking spots available with pricing!

You can also choose if you want in/out garage access. If you know you won’t need to move your car, then choose a garage without in/out access as they’re a bit cheaper.

If you’re looking for parking close to Millennium Park, look at the garage on 180 N Franklin Street. It’s about a mile away and very affordable.

Where to Stay in Chicago

There are tons and tons of hotels to choose from in Chicago. When looking for a hotel, I highly recommend writing down the features and amenities you’re looking for. The hotels in Chicago all offer different amenities, so do your research! Not all hotels offer complimentary breakfast or have a pool.

We knew we’d be spending a majority of our time near Millennium Park and Navy Pier. So, our main goal was to find a hotel within walking distance of these attractions. We chose to stay at the Hilton Garden Inn Chicago Downtown/Magnificent Mile.

There are plenty of other Hilton options around Chicago, but this Hilton was less than a mile away from Millennium Park and was the most affordable at just under $100 for a Saturday night stay. They do not serve complimentary breakfast, but they do have an indoor pool and hot tub.

We stayed in a standard king room on the 17th floor and it was very modern, spacious and clean. I felt very safe and comfortable staying there and will definitely stay here again the next time we come!

Restaurants nearby include: Eataly, Goddess and the Baker, Sugar Factory, Grand Lux Cafe, Shake Shack, Rock Bottom, Beatrix, Rainforest Cafe, McDonald’s, Portillos, Lou Malnati’s, Hampton Social, Starbucks and so many more.

Michigan Avenue was about two blocks from the Hilton Garden Inn Chicago Downtown/Magnificent Mile so there were lots of stores nearby if you love to shop – Nordstrom, Marshalls, TJ Maxx, Loft, Nike, Express, Zara, Under Armour, and more!

Shedd Aquarium

The Shedd Aquarium is a must-see attraction if this is your first time to Chicago. The aquarium houses approximately 32,000 animals from aquatic environments all around the world. There are four floors of tanks full of incredible beluga whales, dolphins, sharks, octopi, stingrays, turtles, snakes, sturgeon and more!

This was our favorite attraction by far! We spent roughly 4 and a half hours there exploring the exhibits and walking around. Depending on the day you visit, there are different shows and speakers you can see. We saw one of their dolphin shows, which was so awesome!

The Bean

Located in Millennium Park, the Bean is a classic photo opportunity in Chicago! It’s incredible. If you want to avoid crowds, you’ll want to visit either early in the morning or at night.

We came here both during the day and then again at night on our walk back to our hotel. We actually enjoyed seeing it at night more, with less people around. You’ll be able to take a better photo without other people being in your shot!

There is so much to see in Millennium Park, so definitely take some time to walk around and look at a few of the statues and displays.

Ice Skating in Millennium Park

Obviously, an activity for the winter, but definitely something you’ll want to add to your bucket list. If you’re a Hilton Hotel guest you actually skate free! Simply show your room key and they’ll hand you a pair of skates! You can also skate free if you bring your own skates, but if you need to rent a pair they’re $15.

It’s so fun to skate at night and see the city all lit up! The rink is pretty big and they’ve got music playing. It’s a fun atmosphere for a date night, night with friends, or some family time!

Grant Park

Another beautiful park in Chicago. Chicago is filled with gorgeous parks and greenery. We walked through Grant Park on our way to the Shedd Aquarium and were able to see Buckingham Fountain, the tennis courts, volleyball courts, baseball diamonds, a dog park, a skate park, and tons of greenery!

This is the perfect place to come in the summer if you’re looking for activities to participate in!

Chicago Riverwalk

The Chicago Riverwalk stretches 1.25 miles along the South bank of the river. There’s lots of bars, cafes, events and boat tours along the river walk making it the perfect place to spend a summer evening!

We came in February, so obviously there wasn’t as much going on, but we’re looking forward to coming back in summer because it is beautiful!

Chicago riverwalk and things to do in Chicago

Navy Pier

In the summer, there’s a lot happening on Navy Pier! Expect to see fireworks, boat tours, music, carnival rides, food stands and more! It’s the perfect spot to hang out with your friends and enjoy some good music on a summer evening.

When we came in February, it was still really beautiful. It was 54 degrees out, with some snow still on the pier. We sat on a bench and soaked in the sun, while admiring the skyline and water!

Navy Pier - free things to do in Chicago

Michigan Avenue shops

There is endless shopping in Chicago! You could spend two full days just exploring all the stores. So, I definitely want to come back with my mom and sisters for a shopping trip. However, my boyfriend and I didn’t do any shopping when we visited Chicago together, just because we had so many other things we wanted to see!

Best Places to Eat in Chicago

Lou Malnati’s Pizzeria

I polled my Instagram audience on their top deep dish pizza recommendations in Chicago and Lou Malnati’s Pizzeria was the most recommended! Located .4 miles away from our hotel, we ate here for dinner Saturday night.

This deep dish pizza was amazing! 10/10 would recommend. I can’t wait to eat here again! Great staff, fun atmosphere and incredible pizza.

Grand Lux Cafe

If you’re looking for a delicious breakfast or brunch option, head to Grand Lux Cafe! A few blocks from our hotel, we ate here Sunday morning. We were seated immediately, the service was amazing, the cafe was gorgeous – the decor and detailing is so elegant, and the food was even better.

I had their French toast served on Brioche bread and my boyfriend had one of their breakfast sandwiches with hash browns. I am not lying when I say this was the best French toast I have ever had. The Brioche bread was thicker and soaked up all the butter and syrup and was literal heaven on earth.

We already said, it’s going to be hard to choose a new brunch place when we come back to Chicago, because Grand Lux was phenomenal!

Steak N’ Shake

Our favorite restaurant in Illinois! We don’t have a Steak N’ Shake in Wisconsin so we always stop here when we go to Illinois. On our way back from Chicago we stopped near Elgin to eat at a Steak N’ Shake. The milkshakes are amazing, there’s always new flavors, the food is great (I always get the grilled cheese and fries), and it’s all super affordable!

We already can’t wait to go back to Chicago! It’s definitely a must-visit city if you’ve never been there before! The shopping, food, attractions.. you will not be disapointed!