48 Hours in Chicago: Things to Do

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June was an up and down month for me. One huge up was that I had the chance to take my first vacation of the year. I went to Chicago for a few days to celebrate my girlfriend’s birthday. The trip was much needed.

It wasn’t either one of our first time in Chicago, but there were still some things that we haven’t done or seen there. In this post, I want to share with you things to do in Chicago. If you only have 48 hours in Chicago, then this post is perfect for you.

Magnificent Mile

If you like to shop you have to check out the Magnificent Mile. It’s a stretch of shopping on N Michigan Avenue. There are 460 retailers on the Mag Mile. They also have three malls in the area as well. They are The Shops at North Bridge, Water Tower Place, and 900 North Michigan Shops. There are also stores such as Levi’s and Niketown Chicago. You can also visit landmarks such as The Wrigley Building.

Three Dots and a Dash

One of my friends suggested that I check this place out. I’m glad I did. Three Dots and a Dash is a tiki bar that’s located in downtown Chicago. It took us a second to find the place because the entrance is in a side alley. This place was nice on the inside. They didn’t have the biggest selection of food, but that’s not their specialty. The drinks are. They had a lot of unique cocktails to choose from. Most of them included some type of rum.

Batter & Berries

Batter & Berries is a restaurant that serves breakfast, brunch, and lunch. They are known for their world-famous French toast. If you plan on going, get there early because they don’t take reservations. They do have a waitlist that you can put your name on. It took us about an hour to get a table, but we were prepared.  Batter and Berries is also a BYOB spot, so you can have a mimosa or some bourbon with your French toast. This is a must-stop if you only have 48 hours in Chicago.


I might as well continue talking about food. Every time that I go to Chicago, I have to visit Giordano’s. They have the best deep-dish pizza that I’ve ever had. A small pie will have you full and it will leave you with a box full of leftovers.  There are several locations to choose from in the Chicago area.

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North Avenue Beach

Believe it or not, Chicago has several beaches. We visited North Avenue Beach for an hour before we left. It was cool relaxing on the beach and seeing Chicago’s wonderful skyline behind you. I wish we had more time to stay out there. If you decide to visit North Avenue Beach, leave your alcohol at home. They have a strict rule on that out there, and you could get locked up.


Chinatown wasn’t too far from our hotel. There’s a lot of shops and restaurants in the neighborhood. One store had various green teas to choose from.  I grabbed a small box to check.

Safehouse Chicago

This place was pretty cool. It was a spy bar and a restaurant. You have to know a password to get in. If you don’t, the person working the front will have you do a “task” to access to the bar area. It won’t be anything too crazy. Once inside, you will see the bar decorated in a spy theme. I felt like 007 in there.


The Chicago Cubs were not in town when we went to Chicago, but I wanted to check out Wrigleyville anyway. (Luckily, I went to a game at Wrigley Field a few years ago). I wanted to get some better pictures of Wrigley and the surrounding area. There are several bars that you can visit in the area to chill and grab a drink. We went to a bar at The Hotel Zachary and lounged for a minute on their balcony right across the street from Wrigley Field. I know that place is jumping when there’s a game going on.

As always, I had a great time in Chicago. I didn’t even get a chance to go to the Navy Pier, the Willis Tower, or Guaranteed Rate Field to see the White Sox play. Those things will be on the list next time.

River and Lake Cruises

Next up on the list of 48 hours in Chicago is to check out a cruise. You can sit back, relax, and appreciate Chicago’s cityscape as much as you can by being out on Lake Michigan and along the Chicago River. There’s a selection of speedboat rides and cruises. The Classic Lake Tour is a 40-minute sightseeing trip. It gives you plenty of time to soak up the sights and enjoy the moment. At the old Navy Training Center on Navy Pier, you can leave on a speedboat for a 75-Minute Architecture Cruise, starting on the lake and then going upriver as far as the Willis Tower. The Chicago River Architecture Cruise has a slower pace. You also get a great view of more than 40 listed landmarks.


For 25 years, the 442-meter Willis Tower was the tallest building in the world and is still the 17th tallest, according to the latest ranking. With the Chicago Skydeck Experience Ticket, you can skip the line and in no time reach the Skydeck 412.4 meters above the west side of the Loop. On the twisty route to the elevator, you can experience the movie describing the 45-year history of the Willis Tower and Chicago’s other architectural wonders. At the end of the fun ride, you’ll be mesmerized by a view extending over 50 miles and four states. You might also experience your stomach flutter or a buzzy feeling at the Ledge of the Skydeck. It is a glass box providing never-before-seen views of the city over a sheer drop of more than 100 stories. If you’re not afraid of heights, this is a must-see if you have 48 hours in Chicago.

Art Institute of Chicago

This art museum is home to three of the most studied and recognized paintings of the last 150 years and amongst the best in the world. These works are Nighthawks, American Gothic, and A Sunday Afternoon on the Island of La Grande Jatte by Edward Hopper, Grant Wood, and Seurat respectively. You can also witness Picasso’s Old Guitarist, it represents a great deal of sorrow and grief.

Outside of Paris, the Art Institute of Chicago has the largest collection of Impressionist and Post-Impressionist paintings. You can enjoy various works done by artists like Monet, Cézanne, Renoir, van Gogh and Toulouse-Lautrec. Also, the modern art from the likes of Jackson Pollock, Warhol, Jasper Johns and Matisse, while the modern architecture and design collection has drawings and models by Frank Lloyd Wright, Le Corbusier and more.

Grant Park

Popularly known as “Chicago’s front yard”, Grant Park fronts the Loop on Lake Michigan and is the city’s major open space. It is 319-acres of lush green space, it is a must-see for tourists and a staple attraction for Chicagoans alike. It contains lots of Chicago’s top attractions like the Maggie Daley Park, Museum Campus Chicago, the Art Institute of Chicago, Millennium Park,  and the epic Soldier Field, home of the Chicago Bears NFL team.

In July, Grant Park hosts the Taste of Chicago Festival, the world’s largest food festival, and in October it is the start and finish line for the Chicago Marathon.

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Millennium Park

This award-winning space was built to represent the new millennium and is the most liked attraction in the Midwest.

The Millennium Park is free to enter and has bold public art, mesmerizing architecture, and some futuristic initiatives. For instance, the 2.5-acre Lurie Garden which is part of the world’s largest green roof, whereas the McDonald’s Cycle Center is a modern indoor bike station that offers rental, repair, and a lot more services for Chicago’s cyclists.

Remember to visit the Jay Pritzker Pavilion, it is Frank Gehry’s renowned outdoor music pavilion and is the showpiece of Chicago’s Millennium Park.

Lincoln Park Zoo

Lincoln Park Zoo is spread across 37 acres and was founded in 1868. It should be appreciated for being one of the few remaining free to visit zoos in the United States. There are more than 1100 animals living here and the habitats are being constantly reconstructed. Their mission is to bring people closer to nature. It provides both indoor and outdoor habitats for ostriches, gazelles, pygmy hippos, giraffes, and many more.

Buckingham Fountain

We’ve made it to the last item on the list of things to do if you have 48 hours in Chicago. Buckingham Fountain is located at the center of Grant Park. The Buckingham Fountain was opened to the public in 1927 and is one of the largest in the world, at almost 8 meters tall. The fountain is sculpted out of Georgia pink marble and contains 5,700,000 liters of water. If you’re there during the day, don’t miss the hourly, 20-minute water show featuring the fountain’s center jet shooting water 150 feet into the air.

Designed by Edward H. Bennett, the fountain represents Lake Michigan and has four sea horses symbolizing the states of Wisconsin, Illinois, Indiana, and Michigan.

Below are some resources that I used.

Uber/Lyft – I used Uber and Lyft to get around Chicago. I spent less than I would have if I rented a car and had to worry about parking and gas. Get $5 off your first ride for Uber & Lyft when you click on the links.

Rakuten – I booked the hotel on Hotwire. Before I did that, I signed in to my Rakuten account and completed the transaction that way. I got $12 cash back deposited in my account for booking it that way. If you don’t have Rakuten, sign up for it today. Use my link here and get $10.

Flights – I booked our flights to Chicago with reward points that I earned with the Southwest Rapid Rewards Card. They have a promo where new cardholders can get $40,000 points when they spend $1000 on purchases in the first three months. Click here to get more information about the Southwest Rapid Rewards Card.

Have you ever been to Chicago? What are some things that you must see if you have 48 hours in Chicago?




  1. Heyyyy! I was actually in Chicago a few weeks ago visiting family. Although I didn’t get to visit everything on your list, I did get to experience a few of the Chicago staples like Giodornos, the Willis Tower, the Patio, Harold’s Chicken and I can’t think of the other places. Much of my trip was eating lol.

    1. Nothing wrong with eating. Chicago has great food.

  2. Those are some great spots to try if you are visiting Chicago. Every time you come back you can do something different. You could never get bored. Great post

  3. We have good friends who moved to Chicago about a year ago, we’ve been meaning to get out there to visit and this is a great list of ideas of what to do when we get there!

  4. Love this list! That’s what I love about bigger cities. There’s always SOMETHING to do, no matter the season.

    1. Agreed. There’s so much to do there.

  5. Looks like a great trip. I will try some of these on my next visit

    1. Cool. Let me know how it goes.

  6. terri carroll says:

    I’m from Gary, Indiana which is only 30 minutes from the South Side of Chi, so I cut my teeth on the city. Make sure you get a good Chicago style hot dog or polish next time you’re there. And Gino’s is killer Chicago Deep Dish, although Giordano’s is more widely known outside the Chicagoland area.

    1. I’ll make sure to try both of them next time.

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