After moving to Indianapolis, many people suggested we do a weekend Chicago trip. Chicago is known for its delicious deep-dish pizza, rooftop bars with breathtaking views, Instagram-worthy restaurants, and tons of shopping opportunities. Having heard so much about Chicago, we decided to add it to our summer bucket list and went for our first trip in July 2022. We wanted to get the most out of our Chicago trip, so I created a 4-day Chicago trip itinerary.
If you’re a first-time visitor to Chicago like we were or just looking for ideas for what to do and where to eat, this 4-day Chicago trip itinerary will help you out.
Best Time to Go to on a Chicago Trip
Driving to Chicago
It took almost three hours to drive from Indiana to Chicago. Driving was easy and it was a straight shot. It’s mostly country until you get to Illinois. Traffic becomes more congested as you approach Chicago.
Prepare yourself for possible delays. If you are right outside the city you may experience traffic jams. When you enter the city, traffic is pretty much like New York City, with bumper-to-bumper traffic. It is definitely a smart idea to have two sets of eyes while driving around the city.
Getting Around Chicago
Sometimes, those map navigation apps can be confusing, and you might have to switch between two apps to double-check your directions. It is a smart idea to download at least two map navigation apps such as Google Maps and Waze when you are walking around the city.
Make sure you invest in high-quality walking shoes. There is a lot of walking in Chicago, as it is a big city. Making sure your feet are comfortable while using your map apps is crucial. We bought Hokas and they were absolutely wonderful to walk around in.
Hotel: Hilton Garden Inn Chicago Downtown RiverWalk
Hotel Location
A reader’s tip: Always verify the street addresses of your destinations at least three times.
There are several Hilton Garden Inn hotels in downtown Chicago within a 10-mile radius. We didn’t know that at first and ended up having to spend extra Uber trips to find the correct Hilton Garden Inn hotel.
4-Day Chicago Trip Itinerary
Day 1:
Bar Avec
Bar Avec had a wonderful view overlooking the downtown Chicago skyline. This is a great place to pre-game for your next bar or dinner reservation. If you’re looking for a couple of quick Instagram pictures, this is the place. I highly recommend that you have a second dinner plan option after visiting Bar Avec.
Michael Jordan's Steakhouse
The Michael Jordan Steakhouse was the perfect place for us to spoil ourselves. It was everything you would expect from a six-time NBA champion. From the ceiling to the carpet, this steakhouse was nothing short of high class. Michael Jordan understood the assignment when he designed this restaurant.
All throughout the restaurant decor, he incorporated his famous Jordan brand patterns. Everything from the food to the décor was a reflection of Michael Jordan’s championship caliber.
Day 2:
Shopping: Magnificent Mile
A walk down the Magnificent Mile is a must-do for all fashionistas and sports lovers. There were a lot of well-known shops lining the street that you could spend hours exploring. We window shopped and stopped at Nike, Hoka, and the Sports Team Shop. The Magnificent Mile offers something for everyone when it comes to shopping.
RIVERWALK
Walking the 3.4 mile Chicago Riverwalk provided us with an opportunity to get our steps in. Along the riverwalk, there were tons of people enjoying the scenic waterfront restaurants, bars, and cafes. Whether it’s day or night, the riverwalk offers dining, entertainment, and other activities such as boat tours and kayaking. Reservations for restaurants or boat tours should be made early, as many places told me they were completely booked on the day of.
Utopian Tailgate
The Utopian Tailgate bar is a rooftop bar that reminds you of a tailgate party. There was a tropical paradise bar inside playing all kinds of party music. The bar had an outdoor area where gigantic games like Connect Four, Jenga, beer pong, and corn hole could be played. If you want some fun and maybe even a little competition with some drinking games, then go to Utopian Tailgate.
There was plenty of Instagram-worthy decor both indoors and outdoors. Lots of wall art, faux flowers, and furniture that made you feel like you were at an adult recess. It was a comfortable atmosphere, not overcrowded. The crowd was friendly, there was plenty of seating, and the vibe was really good.
Food was available, but it was mostly drinking food. We ordered crispy fish sliders on Hawaiian buns, which were tasty. You could choose from a variety of delicious, colorful, fruity summer drinks. There were even pieces of candy in some of the drinks. We tried multiple cocktails such as their Stronger Island, Go Fish, and Daised and Confused. All of the drinks we tried were extremely good. I definitely want to go back to Utopian Tailgate again.
Beatnik
Beatnik West Town is another great Instagrammable restaurant. You feel as if you are in a foreign country when you are there. The experience was like escaping to a tropical bohemian paradise.
It was a nice place to eat dinner with small plates and drinks. We ate light, enjoying scallops and brussel sprouts for our entrees. As for our drinks, we enjoyed chilled coconut cocktails made with rum, pineapple, lime, and ginger. A real coconut was used as the drinking glass, making it an incredibly beautiful drink. However, I don’t know how much alcohol was in it.
Other than that, definitely a fantastic light dinner spot. If you are looking for a fabulous Instagram background, visit Beatnik West Town.
Day 3:
360 Chicago - TILT Ride
Our best view of Chicago came from the 360 Chicago TILT Thrill Ride. You will not find a better view during your Chicago trip than this. This 1000 ft high skyscraper building ride offers a breathtaking view of Chicago and a thrilling TILT ride. If you are looking for some excitement and fun, you should ride the TILT.
After waiting in line, you’ll enter the TILT ride room and for about 2-3 minutes, you’ll be tilted while hanging off the side of the building. Photographers will take photos of you during the ride, which can be purchased afterward for saved memories.
We found the 360 Chicago TILT Thrill Ride to be one of the highlights of our Chicago trip. The TILT ride is a perfect indoor activity that you can do all year round.
Giordano's
As first-timers in downtown Chicago, we wanted to try Chicago-style deep-dish pizza. We decided on Giordano’s after narrowing it down. Our hotel was within walking distance of Giordano’s, so we walked there.
Since each pizza took at least 45 minutes to bake, there was a pretty long wait after we ordered. We ordered their Chicago classic deep dish pizza with pepperoni, mushrooms, green peppers, and onions.
The pizza at Giordano’s was really delicious, but if you are super hungry or have somewhere to be, you might want to go somewhere else. My patience almost ran out during that long wait.
Millennium Park
A must-do Chicago tourist activity is to visit The Bean in Millennium Park. The Bean is located in the middle of the park, making it easy for tourists to take pictures from all angles. It was cool to see this monumental work of art. You could touch the exterior and see your reflection through the extremely shiny surface.
Make sure you bring your iPhone or camera with you if you plan to visit The Bean so you can take cool pictures. Do not hesitate to ask someone to take your pictures if you don’t have a tripod. If you take one for them in return, they are usually more than happy to take your picture.
Ghirardelli Ice Cream and Chocolate Shop
We went to the Ghiradeli Chocolate Shop for ice cream sundaes, shakes, and chocolate to satisfy our dessert cravings.
I ordered the Gold Rush – Caramel Almond Sundae with vanilla ice cream, caramel sauce, sea salt, diced almonds, and whipped cream, topped with a Ghiradeli white chocolate caramel square. I loved it and it satisfied my sweet tooth perfectly.
My husband ordered the Chocolate Lover’s Shake which included chocolate ice cream, and chocolate sauce, topped with whipped cream and mini dark chocolate chips. His shake was rich, thick, and creamy, fitting for a super hot and muggy day in Chicago.
Museum of Illusions
Try the Museum of Illusions if you’re looking for something fun to do in Chicago during a rainstorm. Among the illusions they had, some were simple and some were complicated. Some illusions look like they took no time to see, while others can make you feel like you will fall down if you stare at them too long. Fun, indoor museums like the Museum of Illusions are a great place to kill time between activities.
Day 4:
Leaving Chicago - Truffle Grill
Truffle Grille wasn’t your typical brunch spot. There is no seating inside the restaurant, so it’s like a takeout place. After placing your order, you sit back in your car to wait for the food to be ready, and then you go inside to pick it up.
Things We Didn't Have Time to Do on Our Chicago Trip
Downtown Chicago has a lot to offer. It won’t be long before we’re back again for another weekend getaway to Chicago, since we live so close.
Here’s a list of some of the things we either didn’t get to do or really want to do on our next visit:
Things to Do:
- Wendall Boat Tour
- Starbucks Reserve Chicago Roastery Tour
- More Shopping on the Magnificent Mile
- Eat Dinner on the Riverwalk
Restaurants:
- Honeybear Cafe – Your new neighborhood brunch spot
- Bryn Mawr Breakfast Club – Sweet and savory breakfast favorites
- Chicago Brewhouse Riverwalk – Pub eats, local beer & classic cocktails in a lively, casual setting with a big waterfront terrace
- Wake ‘n Bacon – Best Instagrammable brunch in Chicago.
- Paradise Park – A pizza place and patio
- Cerise Rooftop Bar – Hip hotel venue offering rooftop drinking & dancing with spectacular city views until late
- Pizzeria Portofino – Riverwalk patio pizza restaurant
- Ed Debevics – Chicago’s most famous retro-themed diner
- Phlavz – Restaurant/bar whipping up jerk chicken specialties & other Caribbean-style bar bites.
Final Thoughts for Chicago Trip Planning
For first-timers, Chicago can be overwhelming because there is so much to do from the scenic rooftop bars to the delicious Chicago cuisine. It is my hope that this 4-Day Chicago Trip Itinerary will help you plan your next trip to Chicago knowing you will have a great time and get the most out of your trip. Are you planning to visit Chicago soon? How is your itinerary coming along?
Dee
I absolutely LOVED visiting Chicago, but your blog definitely gives great ideas for my next trip!
Michelle
This is one city I would love to visit! You definitely gave me some ideas !
Alex
GIRL-
Chicago was good to me and my husband when we went for our anniversary a few years ago. It was December, so it was definitely a different vibe- but still great food and sights to see!
Jasmine
Chicago is so nice. Thank you for this run down of your trip. I went to Boot Camp in Great Lakes. But never had the chance to get into the city.
Monica
Such nice tips. I wish I had this itinerary on my first Chicago trip. BTW your curls were poppin sis!
Robea
I absolutely LOVE Chicago, and I always enjoy seeing what others are loving about it as well, there is always something new to find! I will definitely be putting a few of your spots on my next hit up Chicago list!!
Tiffany Carpenter
I’ve always wanted to visit ol Chi-Town especially after my fav President & First Lady came into play! I have heard how dangerous it can be to go there and if being honest that has most certainly played a part in my not going as of yet! I travel a lot with my teen and would never want to put her in harms way over my desire to see a place. You def made it look cool and interesting! I love the statues and now I want to go to MJordans spot! Soooo cool! Will not forget that! Thanks for sharing I do hope to get past my fears and go one day soon! ❤️
Kendra
This right hereeeee!! I’ve been saying I want to go to Chicago all summer but can’t make up my mind because there’s soooo much to do. I’ve never been as a tourist lol only to see family so THIS is helpful!! I’m going this fall and I can’t wait. I’m definitely following up, all this good looking food is calling my name for sure lol
Darlesha
I want to go to that illusions museum. That looks so fun. I went to Chicago for the Beyoncé formation tour but never experienced Chicago for a vacation. You just made me want to go after this winter passes lol.
Thank you for providing all the details of your trip.
Jennifer
I plan to visit here soon !! Thanks for the some great ideas on things to do !!
Shannon Speights
I have never been to Chicago. Definitely want to go. Looks like the you had a fabulous time. Oh & thanks for all the tips. I have heard so much about Hokas. I may have to buy a pair.