The Windy City is home to some great professional sports teams, deep dish pizza, and a history of gangsters. On your weekend getaway, get a taste of everything from city parks and garden conservatories to baseball games and Chicago Style hot dogs. We’ve compiled a list of things to do with your time in the city, so hit the road and bring your sense of adventure because Chicago has so much to offer.


Top 10 Things To Do On A Weekend In Chicago

10. Stroll the Magnificent Mile

The Magnificent Mile in downtown Chicago is one of the biggest meccas of shopping in the U.S. It is located in the Michigan Avenue District of Chicago, beginning at the DuSable Bridge on the Chicago River and ending at E. Oak Street. Along the Mile you will find luxury shops like Giorgio Armani, Burberry, and Chanel. You’ll find fine dining restaurants like Fig & Olive and historic ones like Lawry’s The Prime Rib. You’ll be at the heart of Chicago’s theater and entertainment scene. All in all, the Miracle Mile offers tourists over 460 stores, 275 restaurants, 60 hotels, and entertainment to begin or end any day on the town.

9.Relax in Millennium Park

Perhaps the most photographed attraction in the city, Cloud Gate sculpture (colloquially referred to as “The Bean”) is housed in Chicago’s Millennium Park. The park sits on the shores of Lake Michigan and boasts much more than just the famous sculpture. A 5-acre garden, the Chakaia Booker Exhibition of art, a Goose Island beer stand, visiting food trucks, and outdoor concerts at ay Pritzker Pavilion make this park the place to be in the summer. Winter weather doesn’t stop many visitors, though, because the park also has an ice rink in the colder months situated right next to Cloud Gate. This is definitely a place you don’t want to miss on your getaway.

8. Go to a Cubs Game

Wrigley Field, the home of the Chicago Cubs, is one of the best places to be in the summertime. Wrigley is the second-oldest park in the country, behind the Red Sox’s Fenway Park, and fans keep returning to catch the action inside the park. The history of the park alone is enough of a reason to step inside and catch a game. If you’d rather, Wrigley also offers tours, so you can get a good look at the stadium when it’s not packed with fans cheering wildly for the home team. Make sure to explore Wrigleyville, the neighborhood surrounding the park, while you’re in the area. Bars, restaurants, and sports memorabilia shops line the streets and those who don’t want to pay for tickets to the game can catch it on TV just outside the park. Try Murphy’s Bleachers, a local favorite where you can find plenty of outdoor seating and a great view of the outside of the park.

7. Eat at Superdawg Drive-In

Chicago is known for its Italian food, sure, but its hot dog scene is a whole separate entity. Superdawg Drive-In is, you guessed it, a classic-style drive-in founded in 1948. The original recipe, carhops, and the trademark hot dog logo have remained the same in the joint’s humble beginnings. Customers love the vintage style to everything from interior decorations to the hot dog cartons. Mostly, though, it’s the flavor-packed hot dogs that keep people coming back. The pure beef hot dog on a poppy seed bun is topped with golden mustard, tangy piccalilli, dill pickle, Spanish onions, and a hot pepper. This is a Chicago institution you have to check out!

6. Visit Capone’s Old Hangout

One of Chicago’s oldest bars, Green Mill is known for being the old stomping grounds for American gangster Al Capone, “Scarface”. The bar remained open during prohibition as a speakeasy thanks to a pay-off to the police. It has been a filming location for movies like The untouchables, Thief, and High Fidelity. In addition, the bar has been one of the best places for live jazz music for over 100 years. The story goes that famous jazz musician Joe E. Lewis’s tenure at the Green Mill was the reason Al Capone preferred the bar over his own speakeasy in a basement of a building across the street from it. When Lewis was offered more money to play at another Chicago club and ended his residency at the Green Mill, one of Capone’s men attempted to kill him by slashing his throat and leaving him for dead in his dressing room. Ironically, Lewis survived and Capone’s employee was gunned down later on in life. If you’re looking for a little off-the-beaten-path history, stop in to the Green Mill for a drink.

5. Relax in the Tropics

Okay, so you won’t actually be in the tropics, but Garfield Park Conservatory comes pretty close. With six multi-faceted greenhouses, including a tropical room that’s perfectly humid year-round, and two exhibition halls, there’s plenty to do and see. Tours are offered daily and events like Beer Under Glass and Wine Under Glass are offered annually for adults. Admission to the conservatory is free, as well as parking, so your wallet won’t be hurting after visiting. If you’re visiting in those winter months, this is the place to go to warm up!

4. Walk Chicago’s Pedway

Built as an underground pedestrian system to help alleviate the congested street and sidewalks, the Pedway spans across more than 40 blocks of Chicago, roughly 5 miles of the city. Underground, you will not only be protected from the elements of the season, particularly in brutal winter months, you will also be able to refuel on food and beverage. Sweetwater Tavern, for example, is just steps from an entrance to the Pedway and offers a full bar and menu. The Pedway is perfect for a bitter cold day when you don’t want to be outside much, but still want to see some attractions.

3. Drive a NASCAR Race Car

If you’ve ever wondered what it’s like to be a NASCAR driver, this is your chance. Located just 45 minutes from downtown Chicago, Chicagoland Speedway is an official NASCAR race track. For the beginning driver, there is the option to ride-along with an experienced driver for a varying number of laps. If you want to take the driver’s seat, you can do that, too. Choose the number of laps you want and the course that you’d like and you’re on your way. Don’t forget to buckle up for the ride of a lifetime!

2. Attend a Second City Show

Well-known in the comedy sphere as being the upbringing of many a Saturday Night Live star, Second City is the world’s leading comedy theater and school of improvisation. Attend a show and you may just get your idea put into the act. Improvisers will ask for audience suggestions throughout the show, and if you speak up loud enough, they might just use it to propel their act through the night.

1. Eat Deep Dish Pizza

You can’t visit Chicago without spotting restaurants at every corner offering deep dish pizza. You also can’t visit Chicago without getting some deep dish pizza. Luckily, there are a few places that stand out from the crowd. Lou Malnati’s Pizzeria makes an unbelievable pie. Customers rave about “The Lou”, which has spinach, mushrooms, and sliced roma tomatoes covered with mozzarella, Romano, and cheddar cheese on garlic Buttercrust. Pequod’s Pizzeria, in the DePaul neighborhood of Chicago is another competitor for the best deep dish pizza in Chicago. According to the pizzeria, their crust is caramelized, which, when covered with loads of cheese and toppings, explains why people love this place so much. Milano’s Pizza and Specialties offers yet another option for visitors wanting authentic deep dish pizza. Try their version topped with your favorite ingredients and you won’t be disappointed.


This article was written by Julianne Aiello.