How to Spend a Perfect Weekend in Chicago
Updated: Oct 27, 2022
The ultimate guide to a weekend in the Windy City, including unique architecture, deep dish pizza and Lake Michigan views! Chicago is one of the largest cities in the U.S. and the birthplace of the modern skyscraper. There is always a musical festival, new restaurant, or fun attraction to explore.
Instead of a play-by-play itinerary, I’ve provided a guide with some of my favorite sights and eats for you to pick-n-choose your favorites! Create your own custom weekend in the Windy City.
Where to Stay
Downtown Chicago (aka the Loop) is a great place to start for first-time visitors for its easy access to top attractions and walkability. There are endless places to stay in the Loop or along River North to be minutes from your day’s activities.
Freehand Chicago in River North – a classic 1927 building near galleries, restaurants and bars. The Quad room is a great option for friend groups. The Broken Shaker on site offers excellent cocktails and street-food eats from around the world.
ALOFT River North Downtown – The location is surrounded by good eats, including Beatrix, located just off the lobby. The brunch is a great start to the day or enjoy a cocktail with friends during happy hour. The hotel is pet-friendly and provides early check-in if your flight arrives in the morning!
Hyatt Regency in Downtown Loop – Steps from the Chicago Riverwalk, this hotel is perfectly situated. Near the Navy Pier and Millennium Park, you can enjoy all the comforts of a modern urban getaway. Their suites overlook the Chicago River and include exclusive concierge access.
Where to Eat
Chinatown – Head to Chicago’s Chinatown for elaborately adorned streets filled with traditional specialty shops, eastern Asia souvenirs and family-owned restaurants. I love Happy Lamb Hot Pot for a communal dining experience. You can select your own flavorful broth and high-quality proteins, as well as vegetables and a dipping sauce bar. Afterward, enjoy the complimentary soft serve ice cream.
Deep Dish Pizza – No visit is complete without trying some Chicago-style, deep-dish pizza. There is much competition in the city, but the top three pizzerias (IMO) are: Uno Pizzeria, Lou Malnati’s and Giordano’s. Each slice is absolutely loaded with cheese and toppings. Regardless of which pizzeria you choose, be prepared for leftovers!
Osteria di Eataly – This unique marketplace, café and restaurant has it all! Shop two floors of imported Italian groceries, fresh pasta, wines, and treats while you wait for a table in the restaurant. Sip on wine at one of the counters or an espresso at the café. They also offer various cooking classes.
Girl & the Goat – This West Loop restaurant on Randolph Street has excellent food with bold flavors and an extensive drink menu. Make a reservation or plan to head to a bar down the street while you wait!
Food Tour – Chicago’s Secret Food Tours offer private tours of some of the best eats in the city. Try deep-dish pizza, Chicago-style hotdogs, and the famous Italian Beef sandwich.
Donut Crawl – We created our own donut crawl, stopping at Firecakes Donuts, Doughnut Vault and Do-Rite Donuts & Chicken. All locations are walkable, which you will need to burn off some calories as you make room for the next one!
You can also choose to book a tour with Underground Donut, which includes four stops.
What to See
Architecture Cruise – Wendella offers 90-minute classic Chicago River cruises highlighting the world-renowned buildings and 130-year history.
Lincoln Park Zoo – Get outside and explore the wildlife at the Lincoln Park Zoo. Open year round, the zoo is free and open to the public.
Chicago Aquarium – The Shedd Aquarium one of the best in the country, with beluga whales, rockhopper penguins and rockfish. You can explore the world’s oceans, rivers and lakes all in the heart of Chicago. Plan for a few hours with tickets available online.
Navy Pier – Just a few blocks off Magnificent Mile is the Navy Pier, extending out into Lake Michigan. The pier has great bars, live entertainment, and a huge Ferris wheel. Stroll along the water for excellent views of the Chicago skyline.
Magnificent Mile – This section of Michigan Avenue is the retail center of Chicago. Wander down the street for premier shopping, boutiques and people-watching. The architecture along your stroll is beautiful, including the Tribune Tower and the Chicago Water Tower.
Millennium Park & The Bean – No trip is complete to the city without the iconic shot in front of the Bean (aka Cloud Gate). The structure is over 30 feet tall and looks like a gigantic magic mirror, reflecting the bustling city with no visible seams. Millennium Park has a huge playground for kids, a great dog park and a live music amphitheater. There is also the Crown Fountain with a reflecting pool and endless gardens.
Get Up High – Whether the Willis Tower Skydeck or the 94th floor of 360 Chicago you should definitely see the city from a higher advantage point. Tickets for either can be purchased in advance to secure your entry time. Try to choose a sunset entry for spectacular views of the skyline and perhaps spot surrounding four states. Willis Tower offers the Ledge, all glass floor lookout for those daring enough to step off!
Comedy Show – Check out Second City live every night for the best of improv. Many famous comedians have studied their craft at Second City, including Stephen Colbert, Amy Poehler and Jason Sudeikis. Get tickets in advance.
Wrigley Field – Depending on the season, hit up a Cubs game at Wrigley Field. Even if you don’t want to watch a game, the stadium tour is worth checking out. The ballpark has more than 100 years of history.
Free Walking Tours – Free Tours by Foot offers several walking tours around the city, including unique sights like a Gangster Tour for hidden gems and hired guns. I highly recommend a walking tour at the beginning of your trip as it helps orient you in the city as well as provide some cool tips and historical facts about the city you are exploring. Be sure to tip the guides for their time!
Chicago City Pass – If you plan to visit several attractions, you might consider the Chicago City Pass. You can visit the Shedd Aquarium, Skydeck and Field Museum, as well as two other attractions of your choice.
When to Visit
While there is plenty to do in Chicago year-round, it’s not called the Windy City for nothing. Summer is one of the best (and busiest) times to visit, with outdoor festivals, concerts, rooftop bars and sidewalk patios. Fall and spring are my favorite times to visit, as the weather is usually a little more pleasant, though somewhat unpredictable. September is usually still warm, but not as humid as the summer and the students are back in school, which decreases the crowds.
You can fly into Chicago O’Hare (ORD) or Chicago Midway (MDW) airports. The city has many public transportation options, though downtown is very walkable. You can also grab a cab, use an Uber/Lyft or jump on a water taxi. The ‘L’ train has eight lines that run to most of the suburbs and top city attractions. Take your pick!
Chicago is a great city to explore. But remember, the winds off Lake Michigan can make any time of year feel cooler than the temps suggest. Be sure to pack a sweater or light jacket, even in the summer.