Romantic Getaways in Chicago - Ferris Wheels, Fountains & more

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Romantic Spot in Chicago - Buckingham FountainBuckingham Fountain, one of Chicago's Most Popular Romantic Spots

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By: Greg Mattson, ERV Editor - Updated: Apr 11, 2016   

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.

Best Time for Romantic Getaways in  Chicago: the city is fun year-round, but for outdoor activities, we suggest the obvious: May to October.

Chicago's Top Romantic Places & Things to Do

Ferris Wheel at Navy Pier, ChicagoView of the City from Navy Pier Ferris Wheel
Old Town, ChicagoSpecialty Shops in Chicago's Old Town

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

  • Ferris Wheel, Navy Pier (600 E. Grand Ave) - 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.
  • Chicago Horse & Carriage Tour (806 N. Michigan Ave) - take a downtown and lakefront tour some of the best Chicago sights in a romantic carriage.
  • Explore Chicago's Neighborhoods - Old Town has specialty shops and entertainment clubs, Lincoln Park boasts great views of the city by the water, think street culture fun and buskers in Wicker Park/Bucktown, while Logan Square is late-night eateries & live music.
  • The Signature Lounge, 96th floor, John Hancock Center (875 N. Michigan Ave) - 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 at sunset. If you'd like to have a meal up here earlier than that, see our piece on the restaurant in the Chicago dining section below. Or, if you prefer less to eat & drink and want more of the views, just head down to the 94th floor and the... 
  • TILT at Chicago 360 - as the name suggests, you can see all around Chicago, and then enter a special 8-person compartment (extra $7) where you stand looking straight out while the glass and hand rails tilt 30 degrees forward! Gives you views 1000 ft down, and makes you really feel that you are hanging out in Chicago!
  • Millenium Park Ice Rink (201 E. Randolph St) - 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.
  • Go for Drinks at the Trump Hotel - (401 N. Wabash Ave) - the Rebar Lounge on the mezzanine level of the Trump Hotel is one of Chicago's most romantic bars. The floor-to-ceiling windows display the river & downtown in all it's glory, the cocktails are tasty but not out-of-this-world expensive, and the atmosphere is relaxed and intimate. A date-night favorite for both locals and romantic Chicago getaway visitors.  

Best Places to Propose in Chicago:

  • Buckingham Fountain (301 S. Columbus Dr) - the challenge might be to find a quieter spot, but this huge fountain at the center of Grant Park is an iconic symbol of Chicago, and can be very romantic. In the evening, music and lights accompany the dancing waters.
  • Skydeck Chicago, Sears Tower (233 S. Wacker Dr) - views of 4 different states, and the title as the tallest building in America provide you with some great superlatives to match your big moment! Step out on to their Ledge glass box to get the feel that you are really taking the leap...

Romantic Places to Stay in Chicago

Hotel Palomar

Hotel Palomar RoomRoom at the Hotel Palomar
Hotel Palomar, ChicagoHotel Palomar, A Boutique Hotel in Downtown Chicago

Hotel Palomar Chicago - we spent a weekend here in one of their luxury Jacuzzi suites (one of the largest jetted tubs we have seen in Chicago, or anywhere!). Located in downtown Chicago, and you can walk to dining & shopping on the Magnificent Mile, as well as Memorial Park & Navy Pier. The gorgeous lobby downstairs is the place for their evening wine reception, and there's a rooftop pool & terrace as well.    

  • What Other Couples Said: "Fabulous Anniversary Stay"..."Loved the Room Ambiance & Nightly Happy Hour"..."Beautiful, Spotlessly Clean, Luxury Towels". 2016 Rating* for Romantic Chicago Hotels: 96% of Couples Rate It Excellent/Very Good. (505 N. State St, Chicago IL  312-755-9703)

Hotel Monaco

Hotel Monaco, ChicagoHotel Monaco in Chicago

Hotel Monaco Chicago - another romantic Chicago hotel by Kimpton, this one with views of the River and recently updated rooms and suites. 2016 Rating* for Romantic Chicago Hotels: 94% of Couples Rate It Excellent/Very Good. (225 N. Wabash Ave, Chicago IL  312-960-8500)

Talbott Hotel

Talbott Hotel, ChicagoBeautiful Entry to the Talbott Hotel

Talbott Hotel Chicago - couples rave about this luxury boutique hotel that's close to the Magnificent Mile, dining and the Hancock Center. 2016 Rating* for Romantic Chicago Hotels: 98% of Couples Rate It Excellent/Very Good. (20 E. Delaware Pl, Chicago IL  800-825-2688)

More Romantic Accommodation in Chicago:

Residence Inn Lobby BarLobby Bar - Residence Inn Chicago Downtown
Residence Inn Chicago Hotel RoomRoom at the Residence Inn Chicago Downtown/Loop
  • Chicago's Most Romantic Marriott Hotel -The Residence Inn Chicago Downtown/Loop is loved by couples for it's location, boutique style suites, and cocktails and craft beer on tap in their lobby lounge. 2016 Rating* for Romantic Chicago Hotels: 100% of Couples Rate It Excellent/Very Good. (11 S LaSalle St, Chicago IL  312-223-8500) 
  • Chicago Vacation Rental Condos & Apartments - check out Vacation Home Rental's 2016 selection of the the best short-stay romantic condos and town homes in Chicago. Many come with amenities like full kitchens, high-speed internet, LED TV's, A/C, plus city and lake views.
  • Chicago Whirlpool Tub Suites - if you're looking for a hotel room with a private in-room hot tub for 2, check out our latest listing of hotel suites with hot tubs in both downtown Chicago and the suburbs.
  • Chicago's Top-Rated Hotels - deals and weekly specials at romantic Chicago hotels like the Langham, Hyatt Regency and Trump International Hotel. 

Romantic 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 - around 90 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.

On the weekend, there's Sunday brunch at The Starved Rock Lodge (Routes 178 & 71, Utica, IL), which would also make a fine romantic overnight from Chicago.

Windy City Dining for 2

Signature Lounge Romantic Lunch with a View, ChicagoHigh Up Above Chicago at the Signature Room Restaurant, John Hancock Center
  • The Signature Room, 95th Floor, John Hancock Center - here's a tip you can use, based on what we did to have a very good meal at a reasonable price - with an unbelievably romantic view of downtown Chicago! If you'd like to visit the observation deck of this famous Windy City skyscraper, it costs $18 per person for the lift up. However, if you come up to eat at the restaurant, which is only 9 stories lower, there's no lift charge. So you can put the $36 towards lunch, which is pretty good! Since meal times can get very busy, we opted for a late lunch around 1:45 PM. Did we mention that the views are spectacular?
  • 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)
  • Romantic Chicago Steak Houses - a safe bet is Morton's on State Street (1050 N. State St, the original location!). For more scenery, try Smith & Wolensky (319 N. State St) where window tables serve up pretty nice views of Chicago River. 

More on Chicago Getaways:

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 Kinzie Hotel Romance Package includes a bottle of sparkling Italian wine, chocolate strawberries, evening reception with appetizers and breakfast the next morning. 

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

*ERV Rating: our unique, non-scientific rating formula for romantic hotels which includes:

  • Romantic Amenities: suites with an in-room Whirlpool bath or JACUZZI® Tub, scenic view, fireplace, lounge, etc
  • Location: proximity of hotel to restaurants, pubs, downtown, etc
  • Clientele: demographic the hotel attracts (couples, families with kids, business travelers, etc)
  • Popularity with Couples & Honeymooners: based on variety of social media & crowd-sourced reviews.   

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