Dusk over Buckingham Memorial Fountain in Chicago, Illinois
Buckingham Memorial Fountain in Chicago, Illinois (Brand X)

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Chicago Romance Travel Tips

  • Chicago has no lack of places to propose, so look high and low for the spot that suits you best. Signature Lounge and Signature Room, high up in the John Hancock Center, and Skydeck, with its see-through floor atop Sears Tower, offer the loftiest settings. If you want to be high but not that high, take your honey for a spin on the Ferris wheel at Navy Pier to pop the question. Closer to earth, propose among 1,000 butterflies in the butterfly garden of the Peggy Notebaert Nature Museum, or give your proposal a backdrop of fireworks during a cruise aboard the tall ship Windy.
  • You don't have to empty the bank account to have a good time in Chicago or to impress your sweetheart. Many attractions are both free and fabulous. Lincoln Park Conservatory, Lincoln Park Zoo, and Garfield Park Conservatory are just three of Chicago's freebies that beg to be strolled.
  • The Art Institute of Chicago is one of the finest museums on earth, with a vast collection of artwork capable of inspiring romance. Walk its galleries and lose yourselves in works created by some of the greatest romantics of all—the world's artists.

See more at WhyGo Chicago's Romantic Chicago guide


Romance Overview: Chicago, Illinois

Like Los Angeles, Chicago has beaches—15 miles of them. Like New York, it has a head-turning collection of museums and some of the best chefs and restaurants in the country. Like London, it has a soaring Ferris wheel, which is only right considering that the very first Ferris wheel made its debut in Chicago in 1893. Like San Francisco, Chicago has a compelling history that includes a breathtaking disaster, the Great Chicago Fire, from which it rose anew like a gleaming phoenix. But Chicago also has attributes that are unique to this city by the lake, not the least of which is Sears Tower, the tallest building in the Western Hemisphere at 110 stories and one of the nation's most dramatic locations for a proposal.Read More

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Hotels


The Palmer House Hilton - Hotel

17 East Monroe Street
Chicago60603

Distance: 2.4 mi.
(from destination center)

Hotel Class: 4 class stars

expert favorite hotel
Expert Rated & Recommended
5_0

Elysian Hotel Chicago - Hotel

11 E Walton
Chicago60611

Distance: 3.6 mi.
(from destination center)

Hotel Class: 5 class stars
expert favorite hotel
Expert Rated & Recommended
5_0

Monaco Chicago, a Kimpton Hotel - Hotel

225 North Wabash
Chicago60601

Distance: 2.8 mi.
(from destination center)

Hotel Class: 4 class stars

expert favorite hotel
Expert Rated & Recommended
4_0

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Attractions


Windy

Departing from Navy Pier
600 E Grand Ave
Chicago, Illinois 60611

Distance: 3.6 mi. (from destination center)
Expert Rated & Recommended
4_0

Geja's Cafe

340 West Armitage
Chicago, Illinois

Distance: 4.8 mi. (from destination center)
Expert Rated & Recommended
4_0

The Signature Room at the 95th and the Signature Lounge

875 N. Michigan Ave.
Chicago, Illinois

Distance: 3.6 mi. (from destination center)
Expert Rated & Recommended
4_0

Airports

Major Airports near Chicago

Distance (mi.)
Chicago Midway Airport 6.9map
Chicago O'Hare International Airport 14.6map
Milwaukee General Mitchell Airport 77.2map

Other Smaller Airports near Chicago

Distance (mi.)
Chicago Pal-Waukee Airport 22.4map
South Bend Regional Airport 69.5map
Greater Rockford Airport 78.3map
More Airports

Chicago Romance Advice


Chicago Vacation Rentals

check rates
from: $200

Vacation Home with Hot Tub and Wi-Fi

Bedrooms: 3
Sleeps: 6
Amenities: Air Conditioning, BBQ, Blender, Cable/Satellite TV, Dishes, Fireplace, Hot Tub, Internet Access, Laundry, Patio, TV, Wireless Internet Access
check rates
from: $250

Vacation Home with Full Kitchen, Internet and Garage, Pet-Friendly

Bedrooms: 4
Bathrooms: 2
Sleeps: 10
Amenities: Air Conditioning, BBQ, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Refrigerator, Smoking OK, Stereo, Stove, TV, Toaster
check rates
from: $-1

Vacation Home with Full Kitchen and Wi-Fi

Bedrooms: 2
Bathrooms: 2
Sleeps: 6
Amenities: Air Conditioning, BBQ, CD Player, Cable/Satellite TV, Coffee Maker, Dishwasher, Full kitchen, Internet Access, Linens, Microwave, Phone, Refrigerator, Stereo, Stove, TV, Utensils, VCR, Wireless Internet Access


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