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1-DAY CHICAGO ITINERARY: DOWNTOWN HIGHLIGHTS

From museums to music, downtown Chicago packs in plenty to do right withing the Loop.

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With just one day to explore downtown Chicago, go big then go home with the top sightseeing highlights packed into a 24-hour span. With the Art Institute of Chicago (one of TripAdvisor's Top Three Museum in the World 2013, 2014, 2015, 2016) and Millennium Park (named one of the six Great Places in America by the APA) as the anchors, this 1-day Chicago itinerary explores Chicago's front lawn — aka Grant Park — and the Chicago Cultural Mile (hint: that's South Michigan Avenue).

Mix-and-match from the 1-day Chicago itinerary stops below to create your perfect summer fun combo of restaurants, parks, museums, music clubs and rooftop views. This day trip planner covers the top downtown Chicago highlights, all within walking distance of the Loop and South Loop.

 

STOP 1:  A MUSEUM FIT FOR FERRIS BUELLER 

Art Institute of Chicago

Walking along Michigan Avenue you will first be greeted by two large bronze lions the stand outside the renowned Art Institute of Chicago. If you would like to know what these lions have to say, before entering the museum, swipe your smartphone on a nearby tag and get a ‘call back' from the lions as part of the citywide public art initiative Statue Stories Chicago.

Inside The Art Institute of Chicago explore America's greatest collection of Impressionist paintings, including world-famous works by Monet, Renoir, Seurat and Van Gogh. Then discover the critically acclaimed Modern Wing, home to an extraordinary collection of modern and contemporary masterpieces by Chagall, Dali, Matisse, Picasso, Pollack and more.

 

STOP 2:  A GIANT BEAN & GIANT ROCK WALL

Climbing Wall at Maggie Daley Park

Across the street from The Art Institute is Millennium Park, an unprecedented combination of stunning architecture, sculpture and landscape design. From the towering faces of Crown Fountain to your own face reflected in Cloud Gate, see why Millennium Park tops everyone's bucket list.    

Exit Millennium Park via the BP Bridge, a 925-foot-long winding bridge that provides incomparable views of the Chicago skyline, Grant Park and Lake Michigan. 

On the other side of the bridge sits Maggie Daley Park, a spectacular green space with massive rock climbing walls, mini golf, picnic groves, and an amazing play garden for children. 

 

STOP 3: THESE BUILDINGS TAKE UP WHOLE BLOCKS

Chicago Cultural Center

On the corner of Michigan Avenue and Randolph Street you'll encounter the Chicago Cultural Center, a Neo-Classic landmark which has the largest the Tiffany stained-glass dome in the world. The stunning building is home to musical performances, dance performances, theatre productions, films, lectures, art exhibitions and family events all for free. 

Further down Randolph is Macy's on State Street, another stunning landmark building boasting seven floor of retail space and great dining options. 

Across the way, Block 37 is a five-story modern urban mall boasting its own gourmet food hall Latinicity and new Dine-in AMC Movie Theatre.

 

STOP 4:  INSTAGRAM-WORTHY VIEWS

Cindy's at Chicago Athletic Association Hotel

After your shopping fix, jump over to the architectural stunner Chicago Athletic Association Hotel for some play in the Game Room (think classic rec room favorites like shuffleboard and billiards alongside classic cocktails like the Old Fashioned and High Ball). For some of the best views in the city, head up to Cindy's rooftop terrace, a restaurant and bar with commanding views across Millennium Park, the Art Institute of Chicago and Lake Michigan.

 

STOP 5:  A WATERFRONT LANDMARK

Walking south and east through Grant Park offers equally impressive experiences for your adventure. At the heart of the 319-acre green space is Buckingham Fountain, a Chicago landmark dedicated in 1927. Inspired by the Latona Fountain at the Palace of Versailles, it operates from April to October, with regular water shows and evening color-light shows. 

 

STOP 6:  A THREE-IN-ONE MUSEUM CAMPUS

Museum Campus Chicago

Walking south from the fountain, a path will take you under Lake Shore Drive into Museum Campus, a gorgeous green space directly on Lake Michigan. The Field Museum will be the first museum you encounter and well worth a trip inside. Founded in 1893, The Field Museum has spent more than 120 years in the pursuit of scientific knowledge about the world around us.

On the way in, you can't miss the 40.5-foot T. rex SUE so be sure to stop by to say hello to the largest, best-preserved, and most complete Tyrannosaurus rex ever found.

Next door is the Shedd Aquarium, where you can meet 32,500 creatures from aquatic habitats around the world including beluga whales, dolphins, sea otters, sea lions and penguins inside the Oceanarium. 

Just beyond the aquarium is the Adler Planetarium, which when constructed in 1930 became America's first planetarium. The building is more than a museum; it is a laboratory, a classroom, and a community exploring the Universe together. Each year half a million visitors experience the museum's interactive exhibitions, live planetarium shows, hands-on educational programs, and world-class collections. 

 

STOP 6.5:  MORE INSTAGRAM-WORTHY VIEWS

Chicago skyline from Museum Campus

When you leave the planetarium make sure you have your camera ready because the vantage point from the Adler provides the best panoramic views of Chicago's famous skyline and Lake Michigan. You will quickly realize why Chicago leads the world in architecture and urban design.

 

STOP 7:  TOWERING HEIGHTS

Time to head back into the downtown Loop. Destination? Skydeck Chicago at Willis Tower, the second tallest building in the Western Hemishphere. Climb 103 stories (by high-speed elevator!) and you'll be treated to views in all four directions, looking out as far as 50 miles out. For the most daring, step onto The Ledge, clear glass boxes that hover 1,353 feet above the city.

 

STOP 8:  A MUSIC MECCA, OR TWO

Two neighboring music clubs, one blues and one jazz so take your pick. Buddy Guy's Legends is the home of the blues, made famous around the world by its namesake Grammy-award winning guitarist Buddy Guy. There's live music every night of the week, with free acoustic shows during the lunch and dinner hour as well. Established in 1947, Jazz Showcase has hosted the greatest names in the business and has a seat waiting for you too.

 


Buckingham Fountain
Columbus Dr. and Congress Parkway
Chicago, IL 60603
(312) 742-4847
Skydeck Chicago
233 S. Wacker Dr.
Chicago, IL 60606
(312) 875-9696
Millennium Park
201 E. Randolph St.
Chicago, IL 60601
(312) 744-6050
Macy's on State Street
111 N. State St.
Chicago, IL 60602
(312) 781-1000
Adler Planetarium
1300 S. Lake Shore Dr.
Chicago, IL 60605
(312) 922-7827
Art Institute of Chicago
111 S. Michigan Ave.
Chicago, IL 60603
(312) 443-3600
Shedd Aquarium
1200 S. Lake Shore Dr.
Chicago, IL 60605
(312) 939-2438
Chicago Cultural Center
78 E. Washington St.
Chicago, IL 60602
(312) 744-3316
The Field Museum
1400 S. Lake Shore Dr.
Chicago, IL 60605
(312) 922-9410
Block 37
108 N. State St.
Chicago, IL 60602
(312) 261-4738
Jazz Showcase
806 S. Plymouth Ct.
Chicago, IL 60605
(312) 360-0234
Chicago Cultural Mile Association
410 S. Michigan Ave.
Chicago, IL 60605
(312) 332-9000
Cindy's
12 S. Michigan Ave.
Chicago, IL 60603
(312) 940-3552
Maggie Daley Park
337 E. Randolph St.
Chicago, IL 60601
(312) 742-3918
Buddy Guy's Legends
700 S. Wabash Ave.
Chicago, IL 60605
(312) 427-1190
Latinicity Chicago
108 N. State St.
Chicago, IL 60602
(312) 795-4444
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