Chicago

Romantic Hotels in Chicago

Hotels in Chicago for romantic couples' getaways

Scroll down to see hotels
Filter by:
Hotel Star Rating
≤2345
Guest Rating
Amazing 9+Great 8+Good 7+Pleasant 6+

Best Hotels for Couples in Chicago

Check out our pick of great romantic hotels for your travel
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+

Claridge House

Hotel near Gold Coast,Chicago
Featured facilities: Spa, Bar
Very Good
105 reviews
8.8/10
1 night
From £105
Check Availability
99+

Sable at Navy Pier Chicago, Curio Collection by Hilton

Hotel near Near North Side,Chicago
Featured facilities: Bar
Great
73 reviews
9.0/10
1 night
From £191
Check Availability
99+

Four Seasons Chicago

Hotel near Streeterville,Chicago
Featured facilities: Swimming Pool, Spa, Bar
Great
109 reviews
9.2/10
1 night
From £447
Check Availability
99+

Trump International Hotel & Tower® Chicago

Hotel near River North,Chicago
Featured facilities: Spa
Great
53 reviews
9.2/10
1 night
From £463
Check Availability
99+

LondonHouse Chicago, Curio Collection by Hilton

Hotel near Chicago Loop,Chicago
Featured facilities: Spa, Bar
Great
124 reviews
9.2/10
1 night
From £179
Check Availability
99+

Viceroy Chicago

Hotel near River North,Chicago
Featured facilities: Swimming Pool, Bar
Great
106 reviews
9.1/10
Check Availability
98

Hotel EMC2, Autograph Collection

Hotel near Streeterville,Chicago
Featured facilities: Bar
Very Good
110 reviews
8.9/10
1 night
From £199
Check Availability
99+

The Langham Chicago

Hotel near River North,Chicago
Featured facilities: Swimming Pool, Spa, Bar
Amazing
110 reviews
9.7/10
1 night
From £463
Check Availability
99+

Staypineapple, An Iconic Hotel, the Loop Chicago

Hotel near Chicago Loop,Chicago
In a city chock full of fabulous—cuisine, art, architecture, and shopping—we proudly present Staypineapple Chicago, An Iconic Hotel. Not to be outdone by the amazing city around it, this award-winning hotel is housed in a National Historic Landmark building and is the perfect jumping-off spot for exploring downtown Chicago. Ideally located in the Loop with The Theatre District and Millennium Park just steps away, you are poised to take full advantage of all the city has to offer. Take in the Art Institute of Chicago, shop the glamorous boutiques of the Magnificent Mile, marvel at the details of the Rookery, or cheer along with the crowds at one of the city's many festivals, all before returning to posh accommodations and deluxe amenities. Staypineapple Chicago offers incomparable style, grace, and warmth.
"The hotel is great, especially the location, very close to the attractions, the Millennium Park is 5 minutes walk, the wills sky tower is 9 minutes walk, the Chicago River Cruise is also 10 minutes from the Museum District, 25 minutes, the Navy Pier 32 minutes, in short You don't have to buy a bus card here, walking is enough. Especially to the airport is very convenient, two minutes to the subway blue line directly to O'Hare airport, very convenient. Breakfast has not been eaten. The room was a little bit small, I ignored it, and it was so perfect when I went out. It feels good. Only a little hotel received my estimate of $200 is a deposit. If there is no problem, I will return it. I will ask how long I can return to my account. The front desk said that I don’t know. The money was swiped directly from the credit card. A bit uncomfortable."
Great
107 reviews
9.1/10
1 night
From £140
Check Availability
See All Romantic Hotels in Chicago

Frequently Asked Questions

What is the average price of a hotel in Chicago this weekend?

According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago this weekend is £325 per night. For a 4-star hotel, the average cost is £411 per night. If you're looking for a luxury experience, 5-star hotels in Chicago this weekend typically cost £898 per night.

How much do hotels in Chicago cost per night on weekdays?

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago during weekdays is £269 per night. For a 4-star hotel, you can expect to pay around £364 per night. If you're seeking a luxury stay, 5-star hotels in Chicago generally cost £819 per night on weekdays.

What are the best places to stay in Chicago?

Some of the best places to stay in Chicago are near popular attractions like Millennium Park, Willis Tower and Magnificent Mile, offering easy access to key sights and amenities.

What are the top hotels in Chicago near Millennium Park?

Some of the top hotels in Chicago near Millennium Park include The Palmer House Hilton (from £161), Swissotel Chicago (from £150) and Hyatt Regency Chicago (from £154), all offering easy access to Millennium Park, making them ideal for visitors looking to explore the area.

Which hotels in Chicago are pet friendly?

Aloft Chicago Mag Mile (from £140), Motel 6 Chicago, IL - Halsted (from £59) and Claridge House (from £114) allow pets. Take your pets with you during your stay!

How to get good deals on hotels in Chicago?

To get the best hotel deals, try these Trip.com tips: 1. Log In Trip.com first and unlock member-only rates and Trip Coins (loyalty points). 2. Book Midweek: Sun–Thurs stays are much cheaper than weekends. 3. Set Price Alerts: Monitor price drops and rebook if needed. 4. Use “We Price Match” Policy: If you find a lower price elsewhere, Trip.com will refund the difference. 5. Avoid major holidays, conventions, and big events. 6. Check the Deals Page to see what promotions are available now on Trip.com.