Chicago Romance Travel Guide

Buckingham Memorial Fountain in Chicago, Illinois (Brand X)
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 beaches15 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
Get Advice About Chicago
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Attractions
Windy
Departing from Navy Pier
600 E Grand Ave
Chicago, Illinois 60611
Distance: 3.6 mi. (from destination center)
600 E Grand Ave
Chicago, Illinois 60611
Distance: 3.6 mi. (from destination center)
Expert Rated & Recommended
Geja's Cafe
340 West Armitage
Chicago, Illinois
Distance: 4.8 mi. (from destination center)
Chicago, Illinois
Distance: 4.8 mi. (from destination center)
Expert Rated & Recommended
The Signature Room at the 95th and the Signature Lounge
875 N. Michigan Ave.
Chicago, Illinois
Distance: 3.6 mi. (from destination center)
Chicago, Illinois
Distance: 3.6 mi. (from destination center)
Expert Rated & Recommended
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 |
Chicago Romance Advice
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Top Ten Destination Marathons
Some people's idea of vacation is a weekend spent stagnant next to an infinity pooland there is nothing wrong with that. For others, it means logging some serious miles in crowded city streets, on pink-sand beaches, and through quiet hill country. Here are our picks for top ten destination marathons (with a few other kinds of races sprinkled in) from New York to Paris. Away Top Ten -
Family Travel Survival Guide: Chicago
A family-travel writer based in the Chicago area shares her family fun favorites in the Windy City. Away Travel -
Top Ten North American Train Journeys
For a front-row ticket to North America’s natural beauty, hop a train bounding over majestic mountain peaks, deep lakes, and wide-open prairies. In this case, the best view is from the most outdated seat, and the journey far surpasses the destination. Away Top Ten -
The Top 10 Historic Trails
Experience the rich history of the U.S., from Native American culture and the Civil War, to the gunslingers of the Wild West and the civil rights movement. Away Top Ten -
Top Ten U.S. Art Cities
For a culture-minded vacationwhether you want to admire breathtakingly beautiful art, stimulate your creativity, or get provoked by the edgy and offbeat here's our list of ten don't-miss cities. Away Top Ten -
Top Ten Ways to Survive Winter's Last Blast
When spring is near, but still oh so far away, try one of our favorite late-season trips, and see winter out with a bang. Away Top Ten -
Top Ten 4th of July Celebrations
Celebrate America's Independence Day in style this year. Here, we've picked our ten favorite spots. Away Top Ten -
Top Ten Refined U.S. Music Festivals
Ravinia Festival, Chicago, Illinois. Away Top Ten -
Top Ten Summer Music Festivals
Lollapalooza, Chicago, Illinois. Away Top Ten -
Get Outta Town: Chicago
Escape the Windy City's concrete-and-steel canyons for a drive along the shoreline of Lake Michigan and through some of Chicago's ritziest neighborhoods. Away Travel -
Take Me Out to the Ballpark: Top Ten Baseball Stadiums
Be a part of America's favorite summer pastime and catch a game at one of the country's ten best baseball stadiums, or just check out the sights in these great American cities. Away Top Ten -
Chicago
Kayaking through the Windy City. Away Travel -
The Third Coast
The Best of the Rest: Michigan, Wisconsin, Missouri, & Illinois. Gorp Travel -
November Romantic Travel Guide
Away Travel -
June Culture Travel Guide
Away Travel -
Moveable Feasts
City-Specific Food Tours. Away Travel -
Best Family-Friendly Hotel Chains
Away Practical Advice -
Ultimate Insider Slumber Parties: Museum and Zoo Overnights
Looking for an adventure close to home? Want to dodge the crowds at the country's busiest theme parks? Then spend the night with dinosaurs, sharks, penguins, or Egyptian mummies at the ultimate insider slumber party. Museums and zoos all over the country host sleepovers for families, where fun and education mesh together in an exciting evening adventure. Away Travel -
The Oregon Trail
An historic journey between the Oregon Coast and Provincetown, Massachusetts. Gorp Travel -
Backyard Playgrounds
Chicago. Gorp Top Ten -
Chicago: Top Luxury Attractions
Away Travel -
Chicago: Top Attractions
Away Travel -
Off-the-Rails Adventure
Sailing in Chicago, Illinois. Gorp Travel -
Top Ten Off-the-Rails Adventure
Sailing in Chicago, Illinois. Gorp Top Ten -
Urban Rivers: Southeast
New Orleans, Louisiana. Gorp Travel -
Top Ten Chicago Getaways
Gorp Top Ten -
Mountain Biking the Windy City
Surprising Finds in the Chicago Area. Gorp Travel -
Weekend Wheeling in Chicago
Four Windy City Bicycle Rides. Gorp Travel -
The River-to-River Trail
Hiking in Illinois from the Ohio to the Mississippi. Gorp Travel -
Water Trails of Northeastern Illinois
Canoeing and kayaking near - and even in! - Chicago. Gorp Travel -
Weekend Backpacker: Chicago
Get Away from the Windy City. Gorp Travel -
My Kind of Town
Rounding up favorite outdoor spots in and around Chicago. Gorp Travel -
Water Trails
Eastern and Midwest Water Trails 1. Gorp Travel -
Water Trails
Paddling Paths of America. Gorp Travel -
Family Weekender: Chicago
Family Getaways from the Windy City. Gorp Travel -
Two-Wheel Territory: The Tops in Mountain Biking
Mountain Biking Illinois's Palos/Sag Valley Forest Preserve. Away Trip Idea - + Show more Chicago Romance Advice
Chicago Vacation Rentals
Vacation Home with Hot Tub and Wi-Fi
Bedrooms: 3
Sleeps: 6
Sleeps: 6
Amenities: Air Conditioning, BBQ, Blender, Cable/Satellite TV, Dishes, Fireplace, Hot Tub, Internet Access, Laundry, Patio, TV, Wireless Internet Access
Vacation Home with Full Kitchen, Internet and Garage, Pet-Friendly
Bedrooms: 4
Bathrooms: 2
Sleeps: 10
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
Vacation Home with Full Kitchen and Wi-Fi
Bedrooms: 2
Bathrooms: 2
Sleeps: 6
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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