The Best Romantic Hotels in Chicago, IL from AED 763 in 2026

A river with a yellow boat, surrounded by tall buildings and a bridge.

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Our top choices for Chicago romantic hotels

A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

A modern kitchen with granite countertops, stainless steel appliances, and a central island.

A modern kitchen with dark wood cabinets, a dining area with wooden chairs, and a large flat-screen TV mounted on the wall.

A modern interior with a sofa, chairs, a glass coffee table, and a kitchen area with a grey wall and framed pictures.

1. Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge

Downtown Evanston

Brian W.

AED 773

AED 1,470 total

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with a built-in microwave, stove, and toaster. There is a dining area with a glass table and chairs, and a potted plant on the counter.

A modern living room with a sectional sofa, a glass coffee table, and a blue armchair. There is a potted plant, a painting, and a decorative wall piece.

A modern kitchen with dark cabinets, stainless steel appliances, and a central island with seating.

2. "Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite

Evanston

Angela D.

AED 1,115

AED 2,055 total

includes taxes & fees

25 Oct - 26 Oct

A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

A large bed with a wooden headboard, two bedside tables with lamps, and a window with a view of trees.

A hanging flower basket with purple flowers, a brick wall, and a green lawn with trees in the background.

A room with a desk, a chair, a TV mounted on the wall displaying various streaming services, a window with a blind, and a framed picture on the wall.

3. Master qtr close to nature & easy urban facilities

Riverwoods

Chris F.

AED 393

AED 763 total

includes taxes & fees

27 Oct - 28 Oct

A staircase with a wooden handrail and black metal railings, leading to an upper floor.

A kitchen with wooden cabinets, a white refrigerator, a dining table with chairs, and pendant lights.

A room with a wooden floor, a wooden chair with a cushion, a small table, a clock, and a door leading to another room.

A grassy area with a body of water and trees in the background.

4. Riverfront rental

South Elgin

John V.

AED 643

AED 946 total

includes taxes & fees

1 Nov - 2 Nov

A cozy outdoor hot tub area with a wooden deck, surrounded by a wooden fence and trees.

A cozy living room with a brown leather sofa, a wooden coffee table, and a yellow tray.

A spacious living room with a grey sofa, a coffee table, a TV, and a dining area with a table and chairs.

A snow-covered residential area with houses and street lights.

5. Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

Miller Beach

Carrah D.

AED 440

AED 1,943 total

includes taxes & fees

21 Oct - 22 Oct

View all properties

Top Chicago Hotel Reviews

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Room is spacious, very clean hotel. I would recommend."

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Classy hotel, only great things to say"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Room was small but clean. No housekeeping though for a 3 night stay. Great breakfast Good gym"

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good

"Good property but a very small bathroom and no ho water."

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Quaint lil spot that we came back to after our South Bend visit. Great value and location. Comfy beds and quiet. Also amazing food finds with in walking distance."

Freehand Chicago

10/10 Excellent

"It was comfortable"

Frequently asked questions

Searching for romantic hotels in Chicago?

Are you looking for a romantic vacation? Couples choose Chicago for its popular theater scene and scenic landscape. If you want to spend a romantic day sharing a bottle of wine with your love, you might plan a visit to Lynfred Winery, Valentino Vineyards, or Broken Earth Winery. Whether you and your partner are just looking for a change of scenery or you're you'd like to have specific luxurious amenities, you can choose from 15 hotels and other accommodations in Chicago for the ideal romantic vacation.

What's the best place to stay for a couple visiting Chicago?

Chicago Guest House Wrigleyville is a favorite hotel for couples, and features free WiFi and free parking. Other good choices for a romantic stay include The Neighborhood Hotel - Lincoln Park 303 - Two Bedroom and The Neighborhood Hotel - Lincoln Park 202 - One Bedroom w/ Patio.

How many romantic hotels will we be able to find in Chicago?

Expedia has 15 romantic Chicago hotels for you to get cozy in.

When is the best time of year for a romantic getaway to Chicago?

If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Chicago: The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. Average annual precipitation for Chicago is 50 inches.

What is there to do in Chicago?

There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in Chicago. If you're hoping to experience some of the local culture, you'll love Chicago for its popular theater scene, stunning architecture, and top museums. A visit to Soldier Field, Navy Pier, or Wrigley Field might be just the ticket when you're checking out the sights.

What's the best way to get to Chicago and around town during my romantic getaway?

This information about transportation options in Chicago might help your romantic trip get off to a smooth start: Make your way to Chicago with a flight to Chicago Midway Airport (MDW), which is the closest major airport located 8.6 mi (13.9 km) away. You can take advantage of metro transit at Monroe Station (Red Line), Monroe Station (Blue Line), and Adams-Wabash Station.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Chicago Romantic Hotels

Our top choices for Chicago romantic hotels

1. Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge

2. "Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite