Romantic Places to Visit in Chicago

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Chicago for Couples

Chicago is one of America's most romantic cities. With a great mix of urban and natural beauty, Chicago is the perfect combination of the cosmopolitan and the rustic. Often, the city's skyline is shrouded in clouds, and at night, the lights illuminate the skyline, creating the perfect backdrop for a first date. With plenty of restaurant and theater options, it's easy to find something to do. Or, take a stroll along the waterfront or in one of Chicago's famous parks.
Jay Pritzker Pavilion
Jay Pritzker Pavilion is a stage in Millennium Park that hosts regular concerts and events including the Grant Park Orchestra during the summer months (a series of free concerts). The Chicago Jazz Festival, the Chicago Blues Festival, and Grant Park Music Festival are all held here as well.
201 E Randolph St, Millennium Park, Chicago, IL, 60601
Website
Buckingham Fountain
Buckingham Fountain
This beautiful fountain, dating back to 1927, is one of the largest in the world. Every hour between 8am and 11pm the fountain comes to life shooting 15,000 gallons of water through the air in a dramatic and impressive show. As the day turns dark, lights are added to the show. This is a highlight of a visit to Chicago's famed Grant Park
301 S Columbus Dr, Grant Park, Chicago, IL, 60605
Website
Chicago has plenty more to offer, so see also our other articles: Quintessential Neighborhoods in Chicago and Chicago Bucket List: The Best Places to See.
Navy Pier
Navy Pier
The Navy Pier is one of Chicago's most popular tourist attractions. It opened in 1916 as an amusement and entertainment area and today it includes about 50 acres of gardens, parks, restaurants, shops, and concert venues. One of the most iconic parts of the Navy Pier is the 150 foot ferris wheel, which offers breathtaking views over the city and lake. There's also a classic historic carousel in Navy Pier Park. Head hear to pick up a boat tour as well.
600 East Grand Avenue, Streeterville, Chicago, IL
Website
The Chicago Theatre
The Chicago Theatre
This famous theatre resides in the heart of Chicago. Visitors will be greeted at the entry with the large and frequently photographed "Chicago" sign out front, and then mesmerized by the gorgeous and historic interior with murals on the ceilings and sculptures throughout. The venue puts on a large number of shows from concerts to theatre productions and plays and musicals throughout the year. If you're in town, grab a ticket to any event and you won't be dissapointed.
175 N State Street, Loop, Chicago, Illinois
Website
American Writers Museum
American Writers Museum
Located near Millennium Park, this unique writers museum is the first of its kind in the United States. It offers an overview on the history of American writing including a variety of genres such as fiction, poetry, journalism, and more. It highlights several specific authors and has a number of relics from the history of writing.
180 North Michigan Ave, Loop, Chicago, IL, 60601
Website
Hyde Park
Located on the South Side of Chicago, this neighborhood is rich in history. It was the location of the 1893 World's Fair and it has a number of notable residences including a home designed by Frank Lloyd Wright as well as the former home of President Barack Obama. Hyde Park sits on the edge of Lake Michigan and offers beautiful water views. It's also easily accessible to the 18 mile lakefront running and biking path. Within Hyde Park you'll find the University of Chicago, the Museum of Science and Industry, and part of Jackson Park.
Chicago, IL
Lincoln Park Conservatory
Lincoln Park Conservatory
This impressive Victorian style greenhouse has four separate sections that include the Orchid House, Palm House, Fern Room, and Show House. There's also an outdoor Formal Garden and the English Grandmother's Garden. This is a beautiful conservatory and it's free to the public.
2391 N Stockton Dr, Lincoln Park, Chicago, IL, 60614
Website
Chicago Riverwalk
Chicago Riverwalk
The Chicago River is an iconic part of the city, and it runs parallel to the lakeshore through the heart of the city. The Riverwalk is along a popular stretch of the river, and it's lined with many great restaurants and some of Chicago's most impressive architecture. You can wander along the Riverwalk, rest at one of the many benches, take in the impressive views or simply people watch.
Loop, Chicago, IL, 60601
Website
Interested in more travel advice for Chicago? Check out The Best Science Museums in Chicago and Best Things to do in Hyde Park, Chicago.
Cadillac Palace Theatre
Cadillac Palace Theatre is managed by Broadway in Chicago, and hosts a number of hit shows throughout the year.
151 West Randolph Street, Loop, Chicago, Illinois, 60696
Website
Symphony Center
This music complex is home to the Chicago Symphony Orchestra, the Chicago Symphony Chorus, the Civic Orchestra of Chicago, and the Institute for Learning, Access, and Training.
220 South Michigan Avenue, Loop, Chicago, Illinois, 60604
Chase Promenade
Chase Promenade is a tree-lined pedestrian walkway in Millennium Park. It spans 8 acres and hosts regular exhibitions and festivals.
Chase Promenade Central, Loop, Chicago, Illinois
Civic Opera House
The Civic Opera House is the second largest opera auditorium in the North America. It is the permanent home of the Lyric Opera of Chicago.
20 North Upper Wacker Drive, Loop, Chicago, Illinois, 60606
Website
How much is a romantic trip to Chicago?

Prices for activities, things to do, and tours range from $12 to $24. The average cost for a tour or tickets is $18. A few of the best options are below.

Where to Stay in Chicago

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