Chicago Illinois, or Chitown, is the 3rd-largest city in the US. 55 million tourists visit the Windy City annually. Why? Chicago is full of amazing things to do. To begin with, Chicago has a skyline as impressive as NYC, it borders Lake Michigan, has 24 beaches, 200+ theaters, 55+ museums, 8 major league sports teams, over 75 Michelin-rated restaurants, and the largest Blues Festival in the world. Italian food and Irish Pubs are popular in Chicago, as are deep dish pizza, Chicago hot dogs, Italian Beef sandwiches, and Garrett Popcorn. Keep reading for my detailed Chicago Illinois weekend itinerary including directions.
Did you know the brownie was invented in Chicago? The first skyscraper was built here in 1885 and you can watch the Chicago River flowing backward during your trip. Frank Lloyd Wright’s famous Robie House is here, you can also walk through a neighborhood of middle-class homes he designed in Chicago. Speaking of neighborhoods, there’s everything from Chinatown to Little Italy to Beverly (an Irish neighborhood).
Chicago is full of history and great music. You can attend a blues, jazz, or hip-hop performance any night of the week, or, take a fun mob history tour. There are so many incredible things to do, see, and eat in Chicago it is difficult to decide how to spend your time. Seriously, it is a struggle! Below is how I spent 3 days in Chicago, please use my day-by-day Chicago Illinois weekend itinerary as a template and make it your own by filling in your personal bucket list dreams. Enjoy your time out of the office!
READ 100 Things to Do in Chicago, a Bucket List City
How to Spend a Long Weekend in Chicago Illinois, Weekend Itinerary
Day 1: Italian Beef, Riverwalk, and Art on theMART
Fly into Chicago O’Hare Airport. Grab your luggage and make your way from the airport to your hotel. Take the Blue Line “L” (elevated train) towards La Salle to arrive downtown. The ride is about 45 minutes and costs around $5.00. I stayed at the Cambria Hotel Chicago in the Loop-Theater District and used the Washington exit. The walk to the hotel from the train stop is 2 minutes. Check into your hotel and drop your bags.
Have dinner at Al’s #1 Italian Beef. You may take the 17-minute walk or jump on the Red Line toward Howard at Lake Street, exit at Grand, and walk about 10 minutes.
After dinner walk 10 minutes to Wolf Point West Riverwalk and explore the area walking towards to Wells Bridge. Cross the bridge and backtrack to the Art on theMART viewing platform for the 9-10 PM digital art projection show.
Head to Three Dots and a Dash Tiki Bar for a cocktail, about a 10-minute walk. When you are ready, the hotel is about a 10-minute walk from there.
9 AM Beat the crowds and book an early ticket for Skydeck Chicago. Be sure to step out onto the ledge!
Take the Blue line toward La Salle from Washington to Jackson and walk 8 minutes to the Willis Tower, plan to spend 1.5 hours at Skydeck.
11:45 Book the Shoreline Sightseeing Architecture River Tour for noon (75 minutes).
From Skydeck jump on the Orange or Brown Line at Quincy going toward Midway and exit on State/Lake. Stop for a photo of The Chicago Theatre before making your way to the Riverwalk. Enjoy the views and don’t miss the Tiny Happy Man’s Statues on your way. Also, grab a sandwich and stash it in your bag to eat on the tour.
12:30 Explore the Magnificent Mile
Walk towards the Wrigley Building and onto Michigan Ave, the Magnificent Mile. Be sure to notice the Tribune building as a pass. Do some window shopping as you walk towards the Starbucks Reserve Roastery. Be sure to stop in the largest Starbucks in the world for a coffee and don’t miss the rooftop deck.
3 PM Wander around the Navy Pier
Head towards the water and the Navy Pier stopping at Ohio Beach for photos on the way. Spend some time on the pier, ride the Ferris Wheel, walk out to the observation deck, grab an Original Rainbow Cone (ice cream), shop for souvenirs, and have a drink on the rooftop bar.
5 PM Eat Chicago’s famous deep-dish pizza at Giordano’s
Pre-order a deep-dish pizza at Giordano’s on Navy Pier and enjoy it on the patio.
6:15 PM Catch a show in the Theater District
Make your way to the 7 p.m. show of Drunk Shakespeare. Grab Bus 29 from the Navy Pier to State/Lake (9 stops, 14-minute ride). Alternatively, it is a 30-minute walk or a $15 Uber ride.
10 PM After the show walk 20 minutes to the lakefront trail to watch the 15-minute fireworks show at Navy Pier 10 pm.
TIP: Save money following this Chicago Illinois weekend itinerary by purchasing the Chicago CityPass. Pick 5 attractions and save almost 50%! Options include the Art Institute of Chicago, Shoreline Sightseeing Architecture River Tour, 360 CHICAGO Observation Deck, Skydeck Chicago, Shedd Aquarium, Adler Planetarium, Field Museum, or Museum of Science and Industry. I used it and loved that it told me which attractions required reservations. I saved money and everything was planned ahead of time so I could just enjoy while there.
Day 3: Chicago 360 Observation Deck, Chicago Cubs Game, Buckingham Fountain Light and Water Show
10 AM Book an early ticket for the Chicago 360 Observation Deck to avoid the crowds.
Take the Red Line from Lake Street toward Howard and exit Chicago Street, walk 10 minutes. (make sure to use the “blacklight” function of your camera if it’s an option. Also, turn your flash off and polarizer filter for the best photos)
Note – this is the area with most of the high-end Magnificent Mile shops.
12 PM Spend some time before the game exploring Wrigleyville and have lunch before the afternoon Chicago Cubs game.
Go back to Chicago Street and continue on the Red Line toward Howard to Wrigley Field exiting at Addison.
1:20 PM Catch the Chicago Cubs game
7:30 PM Watch the nightly Buckingham Fountain Light and Water Show. The show begins at dusk every hour on the hour for 20 minutes with the final major display at 10:35 p.m.
After the show make your way to the Harrison Station on State Street and take the Red Line toward Howard exiting Lake Street, walk 1 minute back to the hotel.
Day 4: Shedd Aquarium, Art Institute of Chicago, Chicago Cultural Center
9 AM Book the first entry to Shedd Aquarium.
Take the Red Line from Lake toward 95th/Dan Ryan and exit Roosevelt. Stop to see the Agora Sculpture in Grant Park on your way to spend time with the beluga whales and dolphins. Consider booking an animal encounter.
11:00 AM Grab a Chicago hot dog from the Kim and Carlo’s Hotdog Cart.
Walk through Grant Park towards the Art Institute of Chicago passing Buckingham Fountain on the way, about a 25-minute walk.
12:00 PM See the works of Monet, Van Gough, Picasso, Matisse, Wood, Warhol, and O’Keefe at the Art Institute of Chicago (advance reservation not required). Note: The Art Institute of Chicago is closed on Tuesday and non-flash photography is permitted in all permanent galleries.
Museum highlights include:
- Two Sisters (On the Terrace), Pierre-Auguste Renoir – Gallery 201
- A Sunday on La Grande Jatte, Georges Seurat – Gallery 240
- Étretat: The Beach the Falaise d’Amont, Bordighera and Cliff Walk at Pourville, Claude Monet- Gallery 240
- The Poet’s Garden and The Bedroom, Vincent van Gogh – Gallery 241
- Water Lilies and Houses of Parliament, London, Claude Monet – Gallery 243
- American Gothic, Grant Wood – Gallery 263
- Twelve Jackies, Pat Hearn, Four Mona Lisas and Liz #3, Andy Warhol – Gallery 296
- Portrait of Sylvette David, Picasso – Gallery 390
- Head of a Woman, Man with a Pipe and The Old Guitarist, Pablo Picasso – Gallery 391
- Self-Portrait, Vincent van Gogh – Painting and Sculpture of Europe Regenstein Hall
- Still Life and Nude under a Pine Tree and The Red Armchair, Picasso – Gallery 394
- Daisies and Interior at Nice, Henri Matisse – Gallery 394
- Small Town by Day, Georg Scholz – Gallery 392
2 PM Pass Crown Fountain and Cloud Gate on your way to the Chicago Cultural Center (a 10-minute walk) to see the largest Tiffany stained-glass dome in the world.
3 PM Grab your bags at the hotel (5-minute walk) and head to the airport for your return flight.
Have an extra day? Consider a day trip to Milwaukee! The city is an easy train ride from Union Station. Check out my Milwaukee day trip itinerary.
Be Sure to check the Chicago Board of Tourism website for upcoming festivals, special events, and what’s happening this weekend.
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Chicago Illinois Travel Guide
Pick up an Illinois Travel Guide from Amazon.com to browse on the plane.
Book Your Accommodation in Chicago Illinois Now
Spending the night? Search Booking.com and VRBO in one place to find the perfect property! I recommend staying near the Magnificent Mile, the Loop, or River North. I stayed at the Cambria Hotel in the Loop – Theatre District. It is a mid-priced hotel in a great location.
Chicago Attractions and Day Tours
The best attractions sell out! Don’t chance it, get your tickets now and relax when you arrive.
Travel Essentials
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Have a great vacation!