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Romantic Hotels in Chicago, Illinois

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Top Trending Romantic Chicago Hotels

The Champagne Lodge & Luxury Suites - Willowbrook Hotels
Rating: 3.5 Stars

The Champagne Lodge & Luxury Suites

16 W 621 S. Frontage Rd, Willowbrook - Map
 
 
4.5 out of 5 (681 reviews)
dana hotel and spa - Chicago Hotels
Rating: 4.0 Stars
C$265

dana hotel and spa

660 North State Street, Chicago - Map
 
 
4.5 out of 5 (2,027 reviews)
This downtown Chicago, Illinois hotel is a 4 blocks from Michigan Street and Water Tower and within a mile of Millennium …More
The Peninsula Chicago - Chicago Hotels
Rating: 5.0 Stars

The Peninsula Chicago

108 East Superior Street, Chicago - Map
 
 
4.8 out of 5 (330 reviews)
Radisson Blu Aqua Hotel Chicago - Chicago Hotels
Rating: 4.5 Stars

Radisson Blu Aqua Hotel Chicago

221 N Columbus Dr, Chicago - Map
 
 
4.6 out of 5 (666 reviews)
Situated near the confluence of Lake Michigan and the Chicago River in the Lakeshore East Development Award Winning Aqua …More
Sofitel Chicago Water Tower - Chicago Hotels
Rating: 4.5 Stars

Sofitel Chicago Water Tower

20 E Chestnut St, Chicago - Map
 
 
4.7 out of 5 (2,620 reviews)
The Whitehall Hotel - Chicago Hotels
Rating: 4.0 Stars
C$195

The Whitehall Hotel

105 E Delaware Pl, Chicago - Map
 
 
4.1 out of 5 (3,947 reviews)
Waldorf Astoria Chicago - Chicago Hotels
Rating: 5.0 Stars

Waldorf Astoria Chicago

11 E. Walton Street, Chicago - Map
 
 
4.8 out of 5 (396 reviews)
The Waldorf Astoria Chicago sets a new standard in ultra-luxury experiences, delivering highly refined service in a …More
Hotel Monaco Chicago, a Kimpton Hotel - Chicago Hotels
Rating: 4.0 Stars
C$296

Hotel Monaco Chicago, a Kimpton Hotel

225 N Wabash Ave, Chicago - Map
 
 
4.6 out of 5 (1,482 reviews)
The James Chicago - Chicago Hotels
Rating: 4.5 Stars

The James Chicago

55 East Ontario Street, Chicago - Map
 
 
4.6 out of 5 (2,199 reviews)
Trump International Hotel & Tower Chicago - Chicago Hotels
Rating: 5.0 Stars
C$545

Trump International Hotel & Tower Chicago

401 N Wabash Ave, Chicago - Map
 
 
4.8 out of 5 (1,076 reviews)
This hotel, adjacent to the Magnificent Mile, is located within 2 miles of the Art Institute of Chicago, Sears Tower, and …More

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    Romantic Hotel Guide in Chicago

    Roses are red, violets are blue, isn’t it time for a Chicago trip for two?

    • Uncover the best discounts on romantic hotels in Chicago
    • Choose accommodations with lavish amenities and perks
    • Read verified reviews for advice on the best hotels for you
    Read More

    Chi-Town isn’t just one of the largest cities in the United States; it’s also one of the most romantic.

    Start your couples weekend by checking out one of the city’s signature attractions: the Navy Pier Ferris Wheel. Modeled after the very first Ferris wheel that debuted in Chicago’s 1893 World’s Fair, the Navy Pier Wheel has been a romantic favourite for generations. After the pier, get those creative gears really spinning when you take your partner to the Art Institute of Chicago. The centre spotlights everything from turn-of-the-century photographs, to impressionist paintings, to abstract art. If you and your partner-in-crime love improv, don’t miss a show at the Second City. This legendary improv group is considered a pseudo comedy college for budding stars. Many Second City players move on to television and movie gigs, so catch a performance before they’re gone.

    When it comes to deals on your accommodations in the city, we know discounts are no laughing matter. So book right here on Expedia.ca to find the top discounts on the best romantic hotels in Chicago. Take your pick of rooms and suites with epic window views and special amenities like in-house dining. You can even reserve your stay at a luxury hotel in Chicago, which can include extra perks like in-house spas and valet service.

    Whether you’re on your first big trip together or it’s your anniversary, you can’t go wrong with a romantic trip to Chicago. Take in the sights while saving money on your accommodations. With the cash left over, you’ll have more than enough for an extra trip up the Ferris wheel, hand in hand.

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