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48 hours in Chi-Town
18
items Chicago is one of my favorite places to visit. Its architecture is absolutely stunning and there is so much to do and see. Not to mention the food is amazing. I have never had a bad meal! Follow these recommendations if you are only in Chicago for a ...
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Things to do
FREE things to do
Places to eat
Things to do
Things that you will want to check off your Chicago bucket list before you leave.
360 Chicago has the best views in Chicago. It is even better than the Willis/Sears tower. Its placement in the Magnificent Mile makes it easier to get to as it is conveniently located next to shops and hotels. You will see beautiful views of the city...
360 CHICAGO
The Willis/Sears tower is the third tallest building in the United States and is absolutely stunning. You will get to see the entire city from the top of this building. They also have a sky deck with a glass see through floor for top to bottom views ...
Willis Tower
Stunning views of the city and all of it’s amazing architecture. I do this tour every time I visit because it never gets old. I recommend going at in the afternoon so you can see how it looks during the day, at sunset, and at night. It is cold along ...
Chicago River Boat Architecture Tours
From shopping to restaurants and museums, the Navy Pier is a fun place to spend the day. It is also kid friendly and they have fireworks in the evenings during the warmer months. I didn’t get to ride the Ferris wheel but I’m sure the views of the lak...
Navy Pier
One of the baseball oldest stadiums, home of the Chicago cubs. I would recommend booking a tour here as there is so much history. You’ll want to book on a non game day so you can see the clubhouse and dugouts in person.
Wrigley Field
Catch a water taxi to China town. There’s so many cute shops and great restaurants to try!
Chinatown - Chicago Neighborhoods
FREE things to do
The BEAN! You cannot go to Chicago without visiting this attraction. I recommend going really early in the morning or late in the evening to get good pictures as it can get super crowded.
Cloud Gate
A lively zoo with a variety of different animals. The park is very clean and well maintained. Admission is free!
Lincoln Park Zoo
Although this park is home to the Bean, the park has many other interesting sculptures and fountains to look at that are great for a photo op. They also host many free concerts here in the Summer.
Millennium Park
Chicago has such beautiful architecture! This place is absolutely gorgeous with the most stunning mosaics. You must witness this in person and it is 100% free.
Chicago Cultural Center
Places to eat
The food in Chicago is TOP Tier. You have to try the foods Chicago is known for such as a good deep dish pizza. But it is really impossible to have a bad meal here. So many delicious options.
Great deep dish pizza! You will want to book a reservation or do takeout to avoid the long wait.
Lou Malnati's Pizzeria
Favorite “touristy” place to get deep dish pizza. You will want to book a reservation as the wait in rather long. Also it takes at least 40 minutes for them to make the pizza but it’s delicious and worth the wait!
Giordano's Pizza: Authentic Chicago Deep Dish Pizza
Loved the pan pizza here! The caramelized crispy edges made this pizza absolutely delicious. You cannot come to Chicago without trying!
Pequod's Pizza
You have to try this Chicago style hot dog. A hot dog with a handful of toppings that brings all the flavor.
Portillo's
AMAZING underrated spot! They have two locations with different menus so you’ll want to review the menus on their website before deciding which location to go to. This restaurant is reservation only and has a small but intimate feel. A perfect place ...
The SoulFood Lounge
Grown and sexy steakhouse with good vibes. The music and food were delicious. The drinks were also strong. They gave us a complimentary dessert as we were celebrating our anniversary.
Chemistry Chicago
Really good soul food!
Virtue Restaurant
The McDonald’s at Hamburger University has a global menu with interesting cool items to try that is constantly changing. I had Poutine from the Canadian menu and it was pretty good! I definitely recommend making a stop here on your trip.
I went to McDonald's Hamburger University & Global Menu HQ in ...