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Romantic Getaways in Chicago - Ferris Wheels, Fountains & more

Author: Greg Mattson, Excellent Romantic Vacations Editor

By: Greg Mattson, ERV Editor - Updated: Jan 4, 2023   

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 or nearby that will set the mood for your perfect weekend getaway.

Buckingham Fountain, Chicago ILBuckingham Fountain, one of Chicago's Most Popular Spots

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Here's our guide to fun things 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.

Romantic Places to Stay in Chicago

guesthouse hotel

Suite with a Kitchen at the Guesthouse Hotel, Chicago ILGuesthouse Hotel - Kitchen
Bedroom, Guesthouse Hotel, Chicago ILGuesthouse Hotel Bedroom
  • Guesthouse HotelThis family owned boutique hotel in the historic Andersonville neighbourhood is close to Lincoln Square and lots of great shopping and dining opportunities. Just 1 mile from the shore of Lake Michigan and near an El train station, you can be in downtown Chicago within 22 minutes. Choose from 1, 2 and 3-bedroom suites with kitchens, living and dining rooms, private balconies and full-sized washing machines and dryers. Some include gas fireplaces and soaking tubs. Or splurge on the penthouse suites and enjoy a private rooftop deck with city skyline views. What Other Guests Liked: Fitness room, clubroom and library. 2023 ERV Rating*: 96% - Excellent. Room Prices: From $179/night. (4872 N Clark St, Chicago IL 773-564-9568)

stay pineapple

Stay Pineapple Hotel ChicagoStay Pineapple Hotel, Chicago
Stay Pineapple Chicago Romantic Hotel RoomStay Pineapple King Room ©TripAdvisor
  • Stay Pineapple - Located in a beautifully restored landmark 1895 skyscraper building in the heart of the Chicago Loop. It’s conveniently just across from Millennium Park, and less than 400 feet from the nearest El Train stop. Some suites include views of Lake Michigan and in-room spa treatments are available for a special treat. Wi-Fi, wine hour and morning coffee and tea are complimentary. There’s a modern gym and American restaurant onsite. What Other Guests Liked: Lightweight robes, use of beach cruisers, unlimited bottled water. 2023 ERV Rating*: 90% - Excellent. Room Prices: From $136/night(1 W Washington St, Chicago IL 312-940-7997)

Kinzie Hotel

Front of the Kinzie Hotel, Chicago ILFront of the Kinzie Hotel ©TripAdvisor
Romantic King Suite at the Kinzie Hotel, Chicago ILRomantic Suite, Kinzie Hotel ©TripAdvisor
  • Kinzie Hotel - Romantic travellers in Chicago love the central location of this contemporary boutique hotel near Michigan Avenue and the Loop. It’s a 5-minute walk to the closest El Train stop. Free continental breakfast is served daily on each floor, and an evening reception is held in the lounge. Guests can enjoy a drink and assortment of hors d’oeuvers . A well-equipped fitness center, Wi-Fi and coffee makers are included in your stay, and a virtual, touch-screen concierge on the ground floor gives instant updates on weather, flights and more. (Get a selfie there while you’re at it!) What Other Guests Liked: Upgraded HDTV cable package, historic area maps on the walls. 2023 ERV Rating*: 92%. Room Price: From $134/night(20 W Kinzie St, Chicago IL 312-395-9000)

hotel lincoln

Hotel Lincoln, Chicago ILHotel Lincoln, Chicago ©TripAdvisor
Lincoln Hotel Beautiful King Bed Room in Chicago, IllinoisRoom at the Hotel Lincoln ©TripAdvisor
  • Hotel Lincoln - The tree-lined streets of Lincoln Park are home to this upscale boutique hotel dating back to the 1920s. With vintage vibes and contemporary rooms and suites, you’ll find the perfect fit for a romantic getaway in Chicago. There’s a European-style coffee bar on the lobby level, a restaurant, and rooftop lounge offering panoramic views of the city and Lake Michigan. Bike rentals, rooftop fitness classes and a wine hour are among the freebies here. What Other Guests Liked: Easy access to the park, beach, and zoo. Two blocks from Second City comedy club. 2023 ERV Rating*: 84% - Very Good. Room Price: From $88/night. (1816 North Clark Street, Chicago IL 312-254-4700)

publishing House B&B

Room at the Publishing House B&B, Chicago ILRomantic King Room at the Publishing House B&B, Chicago
  • Publishing House B&BFormerly the Methodist Publishing House, the building dates to 1909, and has been beautifully renovated into an 11 room boutique inn. Located in the West Loop neighbourhood of Chicago, on a tree-lined street, you’ll be a 17-minute walk from the French Market. There’s a bar and communal kitchen as well as a common area with fireplace and piano. Cast iron claw foot tubs, steam showers, heated floors, and automatic blinds are nice touches. What Other Guests Liked: Cozy robes, excellent breakfast. 2023 ERV Rating*: 96% - Excellent. Room Price: From $139/night(108 N May St Level 2 & 3, Chicago IL 312-554-5857)

residence inn chicago

Residence Inn Lobby BarLobby Bar - Residence Inn Chicago Downtown
Residence Inn Chicago Hotel RoomRoom - 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. 2021 ERV Rating* for Romantic Chicago Hotels: 90% - Excellent. (11 S LaSalle St, Chicago IL  312-223-8500) 
  • 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 Vacation Rental Condos & Apartments - check out VRBO's 2023 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.

romantic getaways from chicago

It's easy to find a romantic break close to Chicago - here's some ideas...

Deer Path Inn

Deer Path Inn, an Historic and Romantic Inn Located on Chicago's North ShoreDeer Path Inn is a Wonderful Getaway on Chicago's North Shore
  • Deer Path InnThis award-winning historic hotel located on Chicago’s North Shore was originally built in 1929. Featuring excellent dining and accommodations, it’s perfect for a mini-vacation or one night getaway from the city. Refined rooms have hardwood floors and romantic touches. Some include decorative fireplaces and garden views. What Other Guests Liked: Afternoon tea service, complimentary use of bicycles, English garden. 2022 ERV Rating*: 96% - Excellent. Room Price: From $359/night. (255 E Illinois Rd, Lake Forest IL 847-234-2280)

herrington Inn

Luxury Spa Bath Suite at the Herrington Inn, Near Chicago in Geneva, IllinoisBeautiful Spa Bath Suite at the Herrington Inn, Geneva IL
  • Herrington Inn - Overlooking the Fox River, the charming Herrington Inn has romantic and affordable accommodations with river views, and a lovely garden courtyard. Each room includes a gas fireplace and deep Whirlpool tub as well as cozy robes and slippers. Most also feature private patios or balconies. Breakfast is included and homemade cookies and milk are served in the evening. What Other Guests Liked: onsite restaurant and spa. 2023 ERV Rating*: 86% - Very Good. Room Price: From $179/night(15 S River Ln, Geneva IL 630-208-7433)

Hotel indigo naperville riverwalk

Hotel Indigo Naperville RiverwalkHotel Indigo Naperville Riverwalk
Romantic Room at the Hotel Indigo Naperville RiverwalkRoom at the Hotel Indigo Naperville
  • Hotel Indigo Naperville RiverwalkLocated on the Riverwalk and close to great restaurants and attractions, Hotel Indigo Naperville is a great option for a quick romantic getaway, as it’s a short distance from Chicago. Wi-Fi is complimentary, and there’s a fitness centre, onsite restaurant, and free parking. Rooms feature Keurig coffee makers and room service is available. What Other Guests Liked: Rooftop bar that overlooks city murals, 12:00 noon checkout. 2023 ERV Rating*: 88% - Very Good. Room Price: From $161/night(120 Water St, Naperville IL 630-778-9676)

la banque hotel

La Banque Romantic Boutique Hotel Close to ChicagoLa Banque Boutique Hotel Near Chicago
La Banque Hotel Spa Style BathSpa-Style Bath at the La Banque Hotel
  • La Banque HotelThis historic property was a former bank and now features 18 cozy guest rooms and a French restaurant. It’s perfect for a romantic getaway, and is in a great location for exploring the area on foot. Small shops and restaurants are located nearby, and it’s just a 3-minute walk to Homewood Science Center. Rooms include mini fridges and coffee makers, or upgrade for a walk-in rainfall shower or Whirlpool tub. Parking, breakfast and a glass of bubbly are complimentary, and there’s a 24-hour fitness center. What Other Guests Liked: Easy driving distance to Chicago and suburbans towns nearby. 2023 ERV Rating*: 92% - Excellent. Room Price: From $199/night. (2034 Ridge Rd, Homewood IL 708-798-6000)
  • Chicago's Top-Rated Hotels - deals and weekly specials at romantic Chicago hotels like the Langham, Hyatt Regency and Trump International Hotel. 

Chicago's Top Romantic Places

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 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 - thinking champagne, chocolate strawberries, breakfast and a late check-out? Try the romance packages offered by these Chicago hotels:

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 ratings for romantic accommodation include:

  • Amenities: including 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, business travelers, etc)
  • Popularity: based on social media & crowd-sourced reviews 
  • Value: product offered compared to room rate 
  • Please Note: percentage ratings are not absolute but for comparative use only  

top hotels, getaways & packages on ERV