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A Look at Romantic Getaways in Chicago

Things for Couples to Do on Romantic Getaways in Chicago

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Romantic Chicago Skyline at Sunset

Chicago is a great place for a romantic weekend or vacation!

The windy city has an energetic abundance of interesting diversions, colorful neighborhoods, and great restaurants.

And you'll always find a great hotel or romantic B&B in Chicago that will set the mood for your perfect weekend getaway.

Here's our guide to fun things for couples to do in Chicago. Plan your weekend in advance, or just sleep in late, grab a leisurely breakfast at a nearby bistro, and pick one of the cities vibrant streets for a relaxing stroll.

*New*: Illinois Jacuzzi® Suites & Hot Tub Hotel Rooms in Chicago.

Top Romantic Places in Chicago


For the best romantic getaway in Chicago, try out these activities and attractions:

  • 1. Ferris Wheel, Navy Pier - great spot to enjoy the Chicago Lakefront views and breeze. You can round out the day with dinner at any one of several nearby restaurants, and there's an evening fireworks display in the summer months.

  • 2. Horse Drawn Carriage Tour - at the corner of Michigan & chestnut streets, take a downtown and lakefront tour some of the best Chicago sights in a romantic carriage.

  • 3. The Signature Lounge, 96th floor, John Hancock Center - the martinis are a bit on the pricey side, but the views of the city and the Lake Michigan shore make this one of the most romantic spots in Chicago. Especially romantic at sunset.

  • 4. Millenium Park Ice Rink - from late November till April, you can enjoy free skating on the NHL-size outdoor rink (small charge for rentals). A very romantic winter activity in Chicago.

  • 5. Joseph Petrillo Band Shell - for a romantic Chicago evening in the summer, this is a fine place for a picnic and some classical music outoors under the stars.


Flemish House of Chicago - spend a romantic weekend in a Chicago B&B. Perfect spot for a honeymoon or anniversary getaway in Chicago, IL.

Know of a Really Romantic Chicago B&B, Hotel, Attraction? Tell Us!



Best Places to Propose in Chicago:

Buckingham Fountain at Night, Chicago Buckingham Fountain - the challenge might be to find a quieter spot, but this huge fountain at the center of Grant Park can be very romantic. In the evening, music and lights accompany the dancing waters.

Skydeck of the Sears Tower - views of 4 different states, and the tallest building in America provide you with some great superlatives to match your big moment!

2 Great Day Trips from Chicago

Here's two quick (and cheap!) weekend escapes from Chicago couples will love:

Indiana Dunes National Lakeshore - pack a picnic lunch, and drive 45 minutes southeast of Chicago to the shores of Lake Michigan for hiking, biking, beachcombing, and exploring the wetlands.

Starved Rock State Park - only 28 miles southwest of Chicago. Hike up the rocky bluffs and past waterfalls for great views of the Illinois River, or wander through the little town of Utica. Best time for a visit would be autumn for the fiery foliage. There's Sunday brunch at The Starved Rock Lodge (Routes 178 & 71, Utica, IL), which would also make a fine romantic overnight from Chicago.

For more on ideas and tips on a romantic Illinois vacation, see our section on Romantic Getaways in Illinois

Romantic Hotels in Chicago

There's all kinds of romantic inns and honeymoon hotels in Chicago. So we are putting the final touches on our page on the best romantic hotels in Chicago, including picks for romantic B&B's, resorts, and honeymoon suites. Watch for it soon!

Chicago Hotels - Save up to 50%!

Romantic Dining in Chicago

Don't forget to check the full listings and reviews in our Romantic Chicago Restaurants page . For now, here's some romantic eateries in Chicago not to miss:

  • North Pond - this intimate dining room in Lincoln Park has a wonderful warm fireplace great for cold winter nights. (2610 N. Cannon Dr, 773-477-5845)

  • Spiaggia - great Italian offerings with a fine view of Lake Michigan (980 N. Michigan, 312-280-2750)

  • Le Bouchon - small Bucktown bistro with excellent French dishes, reservations in advance highly recommended (1958 N. Damen, 773-862-6600)

More on Romantic Getaways in Chicago:

Find the Lowest Airfare to Chicago Today - the best deals on the Cheapest Flights to ORD , plus discounts on air & hotel packages.

Chicago Hotel Romance Package - The Amalfi Hotel Romance Package includes breakfast, a bottle of sparkling Italian wine, and even dance lessons for 2 at Arthur Murray!

We've got more on our site on romantic holidays in the Northeast USA:


ChooseChicago.com - official visitor's site for Chicago.

Got a Favorite Romantic Chicago Getaway?

Know of any great spots for couples in Chicago? A small inn or B&B, hotel or attraction that would be great for a honeymoon or getaway?

Please share it with us. We (and our readers) would really like to know!

What is it Called?

What Other Readers Recommend:

Here's what our visitor's say about Chicago's most romantic spots...

Romantic Theme Rooms in Chicago - Hotel Monaco  Not rated yet
Thought you'd like to know about our stay at Hotel Monaco in Chicago. We were booked into the Rock & Roll Suite (My husband did it as a surprise - we were ...


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