Chicago

Romantic Hotels in Chicago

Hotels in Chicago for romantic couples' getaways

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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+

Embassy Suites by Hilton Chicago Downtown River North

Hotel near River North,Chicago
Featured facilities: Swimming Pool, Spa, Bar
Very Good
82 reviews
8.9/10
1 night
From SGD 275
Check Availability
99+

Trump International Hotel & Tower® Chicago

Hotel near River North,Chicago
Featured facilities: Spa
Great
55 reviews
9.2/10
1 night
From SGD 619
Check Availability
99+

The Congress Plaza Hotel & Convention Center

Hotel near Chicago Loop,Chicago
Featured facilities: Bar
164 reviews
7.4/10
1 night
From SGD 305
Check Availability
99+

Swissotel Chicago

Hotel near Chicago Loop,Chicago
Featured facilities: Bar
Great
265 reviews
9.1/10
1 night
From SGD 299
Check Availability
67

AC Hotel Chicago Downtown

Hotel near River North,Chicago
Featured facilities: Swimming Pool, Spa, Bar
Very Good
138 reviews
8.6/10
1 night
From SGD 306
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 SGD 471
Check Availability
84

Nobu Hotel Chicago

Hotel near West Loop,Chicago
Featured facilities: Swimming Pool, Bar
Great
100 reviews
9.3/10
1 night
From SGD 880
Check Availability
99+

Staypineapple, An Iconic Hotel, the Loop Chicago

Hotel near Chicago Loop,Chicago
StayPineapple Hotels are all unique and special. Staypineapple An Iconic Hotel The Loop is waiting for you in downtown Chicago. We are located in a National Historic building that mingles with the loops most legendary architecture entertainment and business centers. There is no shortage of big city energy at our corner of the street. But when you walk through our doors we turn down the hustle and bustle and play up the intimate old world charm.
"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 SGD 287
Check Availability
99+

The Palmer House Hilton

Hotel near Chicago Loop,Chicago
Featured facilities: Swimming Pool, Spa, Bar
Very Good
98 reviews
8.4/10
1 night
From SGD 363
Check Availability
99+

The Ritz-Carlton, Chicago

Hotel near Streeterville,Chicago
Featured facilities: Swimming Pool, Spa, Bar
Great
106 reviews
9.2/10
1 night
From SGD 661
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 SGD 436 per night. For a 4-star hotel, the average cost is SGD 564 per night. If you're looking for a luxury experience, 5-star hotels in Chicago this weekend typically cost SGD 1,430 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 SGD 375 per night. For a 4-star hotel, you can expect to pay around SGD 507 per night. If you're seeking a luxury stay, 5-star hotels in Chicago generally cost SGD 1,291 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 SGD 356), Swissotel Chicago (from SGD 369) and L7 Chicago (from SGD 386), all offering easy access to Millennium Park, making them ideal for visitors looking to explore the area.

Which hotels in Chicago are pet friendly?

Club Quarters Hotel, Central Loop (from SGD 253), Aloft Chicago Mag Mile (from SGD 292) and Best Motel By OYO Chicago I-90 (from SGD 102) 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.