48 Hours in Chicago: Your Perfect Weekend Itinerary

The Windy City. Second City. Chi-town. 

Chicago goes by many names, and for good reason, as it has so much to offer year-round. From the arts and sports to incredible cuisine and top shopping, Chicago is a city for all interests and ages, including children.

Here’s how to get swept up in the Windy City for the perfect 48-hour weekend.

ITINERARY 

Friday

3 PM: Check-In at Club Quarters Hotel, Central Loop

With a fantastic central location, Club Quarters Hotel, Central Loop is the perfect spot for work, vacation, or both. The hotel features a mix of historic architecture and renovated design for guests to stay and play in comfort. Each guest room has stunning city views and is equipped with complimentary high-speed Wi-Fi and smart TVs, plus yoga mats, dedicated workstations, tea and coffee machines, and more.

Situated in the heart of downtown Chicago, Club Quarters Hotel is also just steps away from Grant Park, the riverwalk, museums, events, delectable dining options, and more.

4:30 PM: Take a Walk-Through Millennium Park 

Head on over by foot to get your body moving at Millennium Park. It’s a can’t miss attraction in Chicago with non-stop entertainment year-round. Designed by Frank Gehry, the 120-foot pavilion features a state-of-the-art sound system designed to mimic the acoustics of an indoor theater for outdoor entertainment. Don’t forget to stop by the infamous bean for a photo of your own reflection in this iconic feature. 

7:30 PM: Mangia Italiano at Monteverde

Located in Chicago’s West Loop neighborhood, Monteverde is an Italian restaurant that blends the traditions of Italian culture and cooking with the influences of Chef Sarah Grueneberg’s family heritage and trips from around the world. Using simple, fresh ingredients and hand-made pastas throughout the day, “flour is power” is the buzz phrase at this delectable eatery. 

8 PM: Catch a Laugh at Second City Stand-Up

Get your laugh factor on at this improvisational comedy enterprise. Second City is the oldest improvisational theater troupe to be continuously based in Chicago and a starting point for award-winning and famous actors and comedians, such as Bill Murray, John Candy, John Belushi, Stephen Colbert, Tina Fey, Amy Poehler, and more. Book your tickets in advance to ensure a seat.

Saturday

8 AM: Wake Up with Breakfast at Elephant & Castle

Located in Club Quarters Hotel, Elephant & Castle features pub classics with a British heart. Open daily for breakfast, lunch, and dinner, the restaurant is a longtime favorite of locals and tourists alike. Book Club Quarters Hotels Bed and Breakfast offer to receive a complimentary breakfast at Elephant & Castle each day during your stay.  

10 AM: Tour the Art Institute of Chicago

Get artistically inspired at the Art Institute of Chicago (AIC), as one of the “must-see” museums in the Windy City. One of the many favorites for art and culture, the AIC was founded in 1879 and one of the oldest and largest art museums in the world. Located in Millennium Park, the AIC is home to more than 300,000+ works of artwork in an expansive collection of galleries and halls.

12 PM: Get Spirited at Au Cheval

A diner-style bar and restaurant with a passion for burgers, Au Cheval blends the taste of your traditional diner food with proper pub appeal. The bar packs a punch with its wide variety of cocktails and brews on tap, along with local, domestic, and international beers to keep the bubbles flowing. Reservations are not accepted, so plan accordingly and come early to avoid the crowds.

2 PM: Cruise Chicago by the Water
Book an Architectural Boat Tour along the river as you learn and tour the buildings, structures, and skyline of Chicago. Lasting around 90 minutes long, you’ll see architectural views of the city that are only accessible via the water.

6 PM: Dine In at the Innovative Alinea Restaurant

Chicago truly is a place for eating well when traveling. Named the best restaurant in the world by Elite Traveler, Alinea is known for its innovative cuisine. Choose from three unique dining experiences at the Kitchen Table, The Gallery, or The Salon, each with a fresh take on experience, menus and offerings. It is one of the only 13 restaurants in the United States to earn the coveted Michelin 3-Star rating. 

9 PM: Grab a Nightcap at The Green Mill

End the evening with a visit to another local landmark: The Green Mill. Originally opened in 1907, The Green Mill was known to be a favorite of the infamous Al Capone. Grab a cocktail at this Uptown jazz club and be sure to snap a photo of the flickering marquee in the front on your way out.

Sunday

7:30 AM: Kickstart the Day with HERO Coffee

Located in the Southern Loop, HERO Coffee is a Chicago based coffee brew that is a perfect start to your day. First opening their doors in 2014, HERO Coffee is dedicated to their community with a giveback program donating $1 for each retail or whole bean coffee sale to local Chicago charities. Grab a fresh brewed drip or local latte blend with a morning bagel sandwich and you’re energized to go. 

9:00 AM: Bike, Skate, Walk, or Run The 606

The 606 features a long road of artsy adventure, cultured along your bike, skate, walk or run path. Sitting on one of Chicago’s newer green spaces, the 606 is a 2.7-mile trail and a former railroad line that ran between Ashland Avenue and Ridgeway Street. Now open with 12 different access points at approximately every quarter mile, you can be sure to work up an appetite for the midday ahead.

12 PM: Indulge in Deep Dish

What’s Chicago without indulging in some deep dish? Giordano’s is famed as the “Best Pizza Place in Chicago” so put that to your taste-bud test! Using fresh ingredients with the finest cheeses, they stuff their crusts and pizza with only the best. Notably, their pies are double the weight of competitors, so you’re sure to fill your appetites and get your money’s worth. 

1:30 PM: Get the Best Views of the City at The Ledge
Before heading out, get one last view of Chicago from the best view of the city. The Ledge is an all-glass balcony at the Willis Tower’s Skydeck outside of one of the world’s tallest buildings. From the 103rd floor, you’ll see any last nook and street corner you may have missed this visit to Chicago to start planning your next revisit.