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Romantic Hotels in Chicago, Illinois

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The Champagne Lodge & Luxury Suites - Willowbrook Hotels
Rating: 3.5 Stars
C$123

The Champagne Lodge & Luxury Suites

16 W 621 S. Frontage Rd, Willowbrook - Map
 
 
"Private , secluded"
Loved it, came here for my boyfriends birthday and he was extremely surprised, the steam room was our favorite the hot steam and rain forest shower were amazing we really enjoyed the whirlpool.
tatiana from chicago
dana hotel and spa - Chicago Hotels
Rating: 4.0 Stars
C$160

dana hotel and spa

660 North State Street, Chicago - Map
 
 
Couldn't have been happier. Every person we encountered treated us incredibly.
A Traveller
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
C$491

The Peninsula Chicago

108 East Superior Street, Chicago - Map
 
 
"stayed at Ritz, Penisula beyond that"
From front door to room, room to minibar, minibar to Lobby dining, Lobby dining to The Bar, experience was seamless. 2003 Dom Rose on wine list.
Walt from Scottsdale, Az.
The James Chicago - Chicago Hotels
Rating: 4.5 Stars
C$197

The James Chicago

55 East Ontario Street, Chicago - Map
 
 
"First visit. Great location, great service."
Great stay at the James. Great smaller, boutique hotel in a great location in the heart of River North. Service was great. The bathroom could be a bit bigger, but other than, everything else was great!
A Traveller
The Drake Hotel - Chicago Hotels
Rating: 4.0 Stars

The Drake Hotel

140 E Walton Place, Chicago - Map
 
 
"Wonderful accommodations right off Michigan Ave"
Wonderful experience from the doorman to our valet parking. We could not have had a more pleasant interaction with the staff, starting with the doorman. The restaurant food was excellent, and waitstaff was wonderful. Even when we were leaving, the valet not only had our car ready, with luggage in the trunk, but also escorted my husband, who was using a cane, into the car. We will absolutely stay there again.
Lollykins from Peru, IL
Sofitel Chicago Water Tower - Chicago Hotels
Rating: 4.5 Stars

Sofitel Chicago Water Tower

20 E Chestnut St, Chicago - Map
 
 
"The perfect choice in Chicago"
The best hotel I have stayed in Chicago. Service to customers is outstanding and I was wowed by the front desk staff with their exquisite welcoming. Room was warm, confortable bed, gigantic bathroom, ammenities of all sort: a true example of French taste and attention to detail. Not to mention the excellent price for such a great room and location. A very pleasant experience for a 1 night stay that stands out among all my recent business trips!
Alan from New York
Waldorf Astoria Chicago - Chicago Hotels
Rating: 5.0 Stars

Waldorf Astoria Chicago

11 E. Walton Street, Chicago - Map
 
 
"Wonderful hotel and location!"
It is a charming hotel, with a very nice staff. Unbeatable location, the concierge was very helpful planning everyday, and all the hotel facilities were wonderful. It was quiet and cozy even in this busy time of the year.
Eduardo from Panama, Panama
The Waldorf Astoria Chicago sets a new standard in ultra-luxury experiences, delivering highly refined service in a …More
The Whitehall Hotel - Chicago Hotels
Rating: 4.0 Stars
C$148

The Whitehall Hotel

105 E Delaware Pl, Chicago - Map
 
 
"Nice hotel in downtown Chicago"
Rooms are clean and modern. The Lobby is very classy and competitive with big chain hotels. Half a block away from the Magnificent Mile.
A Traveller
Hotel Monaco Chicago, a Kimpton Hotel - Chicago Hotels
Rating: 4.0 Stars
C$173

Hotel Monaco Chicago, a Kimpton Hotel

225 N Wabash Ave, Chicago - Map
 
 
"Loved the ambiance. Staff was very accomodating."
Very comfortable and lovely ambuance. Will definitely return. Great location and loved the window seats!!
A Traveller
Hotel Chicago Downtown, Autograph Collection - Chicago Hotels
Rating: 4.0 Stars

Hotel Chicago Downtown, Autograph Collection

333 N Dearborn St, Chicago - Map
 
 
Great location. Friendly and helpful staff. Room was very big and loved it. Bed and pillows wonderful.
A Traveller

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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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