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A Look at Romantic Getaways in Chicago

Things for Couples to Do on Romantic Getaways in Chicago

Chicago is a great place for a romantic escape! The windy city has an energetic abundance of interesting diversions, colorful neighborhoods, and great restaurants.

Romantic Chicago Skyline at Sunset

And you'll always find a great little 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.

Top Romantic Places in Chicago

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

Couple at an Amusement Park
  • 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.

    Couple Skating
  • 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.

Chicago Explorer Pass - Lots of romantic fun! Visit the Shedd Aquarium, check out the views from the Sears Tower Skydeck, ride the Hop-On Hop-Off Trolley, take an Architectural River Cruise or Navy Pier Ride Pass

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

A couple of 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, 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:

Best Deals on Chicago Flights & Overnights - There's hundreds of air, hotel and package discounts on Chicago Getaways at Tripadvisor - and, readers reviews to help you decide which hotel is the right one.

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:


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Wishing You Some Great Romantic Getaways in Chicago. Have Fun!

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