A Weekend Getaway in Chicago: The Ultimate 48-Hour Itinerary
Visiting Chicago for the weekend? Whether it's your first time or a return trip, 48 hours in the Windy City can be packed with culture, food, and unforgettable experiences. From iconic landmarks and deep-dish pizza to hidden gems and scenic riverfronts, this itinerary will guide you through the best way to spend a weekend in Chicago.
Day 1: Exploring Downtown and the Riverwalk
Morning: Arrival & Breakfast at Wildberry Pancakes
Kick off your weekend with breakfast at Wildberry Pancakes & Café, a local favorite known for its signature berry pancakes and stuffed French toast.
📍 Location: 130 E Randolph St, Chicago, IL
🔗 Visit Wildberry Pancakes
Late Morning: Millennium Park & The Bean
Head over to Millennium Park to see the iconic Cloud Gate (The Bean) and take in the city’s skyline. Walk over to Crown Fountain and Lurie Garden for a scenic start to your day.
📍 Location: 201 E Randolph St, Chicago, IL
🔗 Explore Millennium Park
Late Afternoon: The Art Institute of Chicago
Explore one of the best art museums in the world, home to famous works like Grant Wood’s “American Gothic” and Monet’s Water Lilies.
📍 Location: 111 S Michigan Ave, Chicago, IL
🔗 Visit the Art Institute
Evening: Dinner & Nightlife in River North
For a trendy dinner, head to RPM Italian, a chic restaurant known for its handmade pasta and celebrity sightings. Afterward, grab a drink at a rooftop bar like LondonHouse Chicago for stunning city views.
📍 Location: 52 W Illinois St, Chicago, IL
🔗 Visit RPM Italian
📍 Location: 85 E Wacker Dr, Chicago, IL
🔗 Visit LondonHouse Rooftop
Day 2: Neighborhoods, Museums, and Foodie Stops
Morning: Brunch at The Bongo Room
Start your second day with a delicious brunch at The Bongo Room, famous for its decadent pancakes and creative omelets.
📍 Location: 1470 N Milwaukee Ave, Chicago, IL
🔗 Visit The Bongo Room
Mid-Morning: Explore Lincoln Park & The Zoo
Head north to Lincoln Park, where you can walk through the Lincoln Park Conservatory and visit the Lincoln Park Zoo—one of the oldest free zoos in the country.
📍 Location: 2001 N Clark St, Chicago, IL
🔗 Explore Lincoln Park Zoo
Lunch: Chicago-Style Hot Dog at Portillo’s
For a quick and classic Chicago-style hot dog, visit Portillo’s and grab one "dragged through the garden" with all the traditional toppings—just no ketchup!
📍 Location: 100 W Ontario St, Chicago, IL
🔗 Visit Portillo’s
Afternoon: Museum of Science and Industry or Field Museum
Depending on your interests, visit either:
- Museum of Science and Industry for interactive exhibits on space, weather, and technology.
🔗 Visit MSI - Field Museum to see Sue the T. rex and ancient Egyptian artifacts.
🔗 Visit The Field Museum
Late Afternoon: Shopping on the Magnificent Mile
Stroll along Michigan Avenue, also known as The Magnificent Mile, to browse designer shops and iconic Chicago retailers like Water Tower Place and The Shops at North Bridge.
📍 Location: North Michigan Ave, Chicago, IL
🔗 Explore Magnificent Mile
Evening: Sunset at Navy Pier & Dinner at Giordano’s
Finish your weekend with a walk along Navy Pier, where you can ride the Centennial Wheel for breathtaking views of the Chicago skyline. For dinner, enjoy a second take on deep-dish pizza at Giordano’s.
📍 Location: 600 E Grand Ave, Chicago, IL
🔗 Visit Navy Pier
📍 Location: Multiple locations across Chicago
🔗 Visit Giordano’s
Final Thoughts
Two days in Chicago is just enough time to see the city's highlights, indulge in famous food, and experience world-class culture. Whether you’re admiring art, cruising the river, or enjoying a slice of deep-dish pizza, this weekend getaway guide ensures you make the most of your 48 hours in Chicago.
For more Chicago travel tips, check out our Must-Try Restaurants in Chicago and Best Things to Do in Illinois.
