Chicago is a fantastic city to explore over a three-day weekend. This itinerary is a perfect mix of tourist attractions with hidden gems, showcasing the diverse neighborhoods of Chicago.
As someone who has lived in the city for over a decade, I continually discover new and familiar aspects to enjoy about Chicago attractions and the many things to eat, see, and do.
Whether you’re a first-timer to Chicago, showcasing the city to visiting family, exploring solo, or searching for hidden gems, this guide will help you make the most of your Chicago experience.
Day-to-Day Chicago Itinerary
Day One: Friday
Morning
Start your adventure at Millennium Park. Snap photos at Cloud Gate (The Bean), and stroll through the neighboring parks, Maggie Daley and Grant Park. Then, head to the Art Institute of Chicago to admire masterpieces from the world’s top art museum. If art is not your thing, check out Museum Campus. Choose from the Field Museum, Shedd Aquarium, or Adler Planetarium.
Afternoon
Take a scenic walk along the Magnificent Mile. You’ll find affordable lunch spots, designer shopping, and plenty of Garrett Popcorn Shops to choose from. Stop by for the famous Chicago mix, it is worth it! Then, continue to 360 Chicago in the John Hancock Building. Test your bravery on The Tilt, a glass enclosure that leans you over the edge for thrilling views of the city below. While at 360 Chicago, visit CloudBar to sip cocktails with breathtaking views.
Evening
Afterward, make your way to the Navy Pier. This family-friendly entertainment district on Lake Michigan offers plenty to do: ride the Centennial Wheel for stunning skyline views, explore shops, dine at a waterfront restaurant, experience Flyover, or catch a movie. End the night with a Chicago-style deep-dish pizza, you can’t go wrong with these classic recommendations.
Day Two: Saturday
Morning
Start your day with a hearty breakfast. Popular places include Meli Cafe, Lou Mitchell’s, Yolk, and Wildberry Cafe.
Afternoon
Hop on the CTA, bike, drive, or ride share to a different neighborhood and explore more of Chicago’s local culture and hidden gems. Here are some fantastic options:
- Hyde Park: Visit the Museum of Science and Industry, walk through the University of Chicago campus, shop on 53rd St, and dine at Virtue Restaurant.
- West Loop: Stroll down Randolph Street, known as “Restaurant Row,” for excellent dining options. Explore several blocks of murals on Hubbard, and hang out at Soho House.
- Wrigleyville: Grab a drink at the bar of your choice—this neighborhood is known for having an atmosphere for every type of drinker. If you’re looking for other entertainment options, check out an improv or sketch comedy show.
- Chinatown: Enjoy authentic Chinese cuisine, shop for unique souvenirs, and walk through Ping Tom Memorial Park for great city views.
Evening
After spending time in one of Chicago’s 77 neighborhoods, continue your evening with a night out on the town. There are plenty of things to do after dark. From famous jazz clubs in Uptown to indoor interactive activities like The Escape Game in River North, you’ll find a nightlife scene for any vibe.
Day Three: Sunday
Morning
Start your morning at your pace and enjoy a leisurely Sunday in the city. The best Sundays include brunch in Chicago. Even better if they’re bottomless. There are plenty of good options to choose from, especially if the options are from our list. Start your Sunday with a quintessential Chicago experience: a bottomless brunch. The city is known for its vibrant brunch scene, offering everything from classic pancakes and eggs to indulgent, creative dishes.
Afternoon
Once you’ve enjoyed your bottomless brunch, take advantage of one of the many free and cheap activities and events in Chicago. No matter the season, there is something to enjoy.
- During the summer, attend a free, annual neighborhood street festival.
- In the winter, head to a holiday market like Christkindlmarket.
- Year-round, enjoy a sports game. Catch the Cubs at Wrigley Field the Bulls or Blackhawks at the United Center and the Bears at Soldier Field
If you skipped earlier attractions, consider revisiting them and saving money on admission by using the GoCity pass. If you’re tired of walking, take a Big Bus or Architecture Tour to see the sights.
Evening
No matter your craving, you’ll have plenty of options for dinner in Chicago neighborhoods. End your last night in Chicago with the best food. Sample tacos in Pilsen, soul food in Bronzeville, or even Michelin-starred dining in the West Loop. Whether you’re craving affordable eats or a high-end tasting menu, Chicago has something for every type of taste bud.
Chicago 3-Day Itinerary FAQ
Q: What is the best way to get around Chicago?
A: The CTA Ventra pass ($5 for a day or $15 for three days) makes getting around the city simple and cost-effective. Rental bikes and scooters are also widely available.
Q: Is 3 days in Chicago enough?
A: While 3 days gives you a great taste of the city, you’ll leave with a list of things to do on your next visit.
Q: Are reservations required in Chicago?
A: For popular restaurants, attractions, and tours make sure you plan to get the best experience.
Q: What food is Chicago known for?
A: Chicago is known for many different types of food including the Chicago-Style Hot Dog, Deep-Dish Pizza, Italian Beef Sandwich, Jibarito (Puerto Rican plantain sandwich), Mexican Food (authentic and uniquely Chicago-style).
Q: Is Chicago safe for solo travelers?
A: Yes! While the city is lively, most people mind their own business. Stay alert as you would in any major city, but overall, it’s a safe destination.
Q: Where can I stay in Chicago during the weekend?
A: For first-timers, I recommend staying in The Loop. Book a hotel in this central location to easily access most attractions. Stay at downtown options like the Palmer House, Aloft Chicago Mag Mile, or Canopy by Hilton Chicago Central Loop. Discover more hotel and lodging options here.
Conclusion: Spending Three Perfect Days in Chicago
This Chicago travel guide is filled with attractions that tourists and locals can both appreciate. If you’re looking for a well-curated itinerary packed with activities, this is the perfect one for you. Regardless of the season, you’ll discover plenty of fun indoor activities, classic Chicago cuisine, world-class museums, and a variety of free things to enjoy.
I hope this guide gives you a taste of all the wonderful experiences Chicago has to offer and inspires you to come back time and time again.
Ready to plan your Chicago trip?
