Chicago

Romantic Hotels in Chicago

Enjoy the most Romantic stays for couples escapes in Chicago.

Swipe down to view more
Filter by:
Hotel Star Rating
≤2345
Guest Rating
Amazing 9+Great 8+Good 7+Pleasant 6+

Best Romantic Hotels in Chicago

Find your perfect Romantic couples' retreat in Chicago.
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Hotel near Streeterville,Chicago
Featured facilities: Bar
Very Good
48 reviews
8.7/10
1 night
From $113
Check availability
99+
Hotel near O'Hare,Chicago
Featured facilities: Spa, Bar, Bathtub
Very Good
249 reviews
8.5/10
1 night
From $176
Check availability
99+
Hotel near Chicago Loop,Chicago
Great
117 reviews
9.0/10
1 night
From $36
Check availability
99+
Hotel near Streeterville,Chicago
Featured facilities: Bar
Very Good
399 reviews
8.6/10
1 night
From $111
Check availability
99+
Hotel near Chicago Loop,Chicago
Featured facilities: Bar
Very Good
135 reviews
8.7/10
1 night
From $253
Check availability
99+
Hotel near River North,Chicago
Featured facilities: Spa
Great
56 reviews
9.2/10
1 night
From $502
Check availability
99+
Hotel near River North,Chicago
Featured facilities: Pool, Spa, Bar
Very Good
275 reviews
8.7/10
1 night
From $103
Check availability
99+
Hotel near Chicago Loop,Chicago
Very Good
92 reviews
8.3/10
1 night
From $137
Check availability
99+
Hotel near River North,Chicago
Featured facilities: Pool, Spa, Bar
Very Good
85 reviews
8.9/10
1 night
From $128
Check availability
99+
Hotel near Streeterville,Chicago
Featured facilities: Pool, Spa, Bar
Great
109 reviews
9.2/10
1 night
From $615
Check availability
Show More Romantic Hotels in Chicago

What's new in Chicago

Updated on October 29, 2026

Navy Pier Winter Fireworks Show

The spectacular, free, and award-winning fireworks display at Navy Pier returns for winter 2026! Experience the magic of winter fireworks every Saturday night at 8 p.m.! Enjoy a comfortable evening on the pier, watching the dazzling fireworks and breathtaking city skyline views!

Navy Pier’s Winter WonderFest

Winter Wonder Festival at Navy Pier — Chicago Holiday Experience Winter Wonder Festival: Experience magical holiday fun at Chicago's Navy Pier with a stunning 42-foot Christmas tree, thrilling rides (Cliff Drift, Zero Gravity, bumper cars), ice skating, and seasonal attractions for all ages.

The Wintrust Magnificent Mile Lights Festival

Wintrust Grand Parade of Lights — 35th Annual Wintrust Grand Parade of Lights: America's largest nighttime parade on November 21st featuring Mickey and Minnie Mouse, Disney floats, marching bands, Santa, the Wintrust Fireworks Show, and millions of lights along North Michigan Avenue!

Frequently Asked Questions

What is the average price of a hotel in Chicago for 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 $279 per night. For a 4-star hotel, the average cost is $373 per night. If you're looking for a luxury experience, 5-star hotels in Chicago this weekend typically cost $1,001 per night.

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

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago during weekdays is $243 per night. For a 4-star hotel, you can expect to pay around $333 per night. If you're looking for a luxury stay, 5-star hotels in Chicago generally cost $910 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 best family-friendly hotels in Chicago?

Families visiting Chicago often prefer hotels like Warwick Allerton Chicago (from $99), HI Chicago Hostel (from $42) and Best Western Grant Park Hotel (from $144), which are well-known for their family-friendly features of spacious family rooms and child-friendly services.

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 $170), Swissotel Chicago (from $172) and L7 Chicago (from $151), all offering easy access to Millennium Park, making them ideal for visitors looking to explore the area.

What are the best pet-friendly hotels in Chicago?

What are the best hot spring hotels in Chicago?

Interested in hot springs hotel as a travel stay? Hilton Chicago (from $172) and Holiday Inn CHICAGO O'HARE AREA by IHG (from $122) offer great hot springs.

What hotel deals are available in Chicago?

Trip.com offers multiple promotions and discounts all year round for both new users and loyal customers . Please check the promotions page to see what promotions are available now on Trip.com.