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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
 
 
"Awesome time! "
I loved everything about this facility. Very quiet and I love the location.
A Traveller
dana hotel and spa - Chicago Hotels
Rating: 4.0 Stars
C$179

dana hotel and spa

660 North State Street, Chicago - Map
 
 
"Good hotel off strip"
Overall a good hotel, very much a boutique type of place. Although the first night was annoying due to a floor fan running all night drying something the rest of the stay was nice. Employees were friendly and helpful. The spa was awesome.
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$441

The Peninsula Chicago

108 East Superior Street, Chicago - Map
 
 
"Our stay was great. "
Staff was awesome. Hotel room was great. Our TV in our bathroom did not work. Everything was great
Traveller from catlin, il
The James Chicago - Chicago Hotels
Rating: 4.5 Stars

The James Chicago

55 East Ontario Street, Chicago - Map
 
 
Modern facilities. Convenient location. Recommendable.
A Traveller
The Drake Hotel - Chicago Hotels
Rating: 4.0 Stars

The Drake Hotel

140 E Walton Place, Chicago - Map
 
 
Beautiful lobby. Tired room. Good location. Best for adults.
A Traveller
Sofitel Chicago Water Tower - Chicago Hotels
Rating: 4.5 Stars

Sofitel Chicago Water Tower

20 E Chestnut St, Chicago - Map
 
 
"Great hotel, perfect location"
Lovely hotel in the heart of Chicago. You can walk to great restaurants and all of the shopping on Michigan Ave and Rush.
Traveller from Miami
Waldorf Astoria Chicago - Chicago Hotels
Rating: 5.0 Stars

Waldorf Astoria Chicago

11 E. Walton Street, Chicago - Map
 
 
"Best Hotel I have experienced"
My favorite hotel in Chicago. Great location and impeccable accomadations. I take my wife here for special occasions as often as I can.
Traveller from Chicagoland
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$188

The Whitehall Hotel

105 E Delaware Pl, Chicago - Map
 
 
"will always stay here"
Con: The only con we had was the bathroom. It was small and when you turned on the shower it squealed at you. I imagine the reason for the small bathroom was due to the overall age of the building and back then they didn't make much room in the bathroom. It's also likely why the shower would squeal. A large bathroom area isn't necessary so it's not a make or break for us. We loved staying here. It's within walking distance to several shops, restaurants, Sears Tower (Hancock Building) and Water Tower Place. We used Lyft or Uber to get around and they came very promptly to the hotel front. Valet parking was wonderful and the staff was always very friendly and helpful. We will ALWAYS stay here when we visit Chicago.
Traveller from Louisville, KY
Hotel Monaco Chicago, a Kimpton Hotel - Chicago Hotels
Rating: 4.0 Stars
C$213

Hotel Monaco Chicago, a Kimpton Hotel

225 N Wabash Ave, Chicago - Map
 
 
"Best hotel stay I've had in a long time"
We had such a lovely stay here. The staff were friendly, welcoming and helpful. Sheila and Richard were extremely helpful in helping me to arrange a birthday surprise for my husband even before we arrived in the hotel. The room was spacious, clean and comfortable, offering a range of services and little additional touches. This was the best hotel stay I've had in a long time.
Traveller from London
Hotel Chicago Downtown, Autograph Collection - Chicago Hotels
Rating: 4.0 Stars
C$155

Hotel Chicago Downtown, Autograph Collection

333 N Dearborn St, Chicago - Map
 
 
Great location, staff terrific. Under construction at the time so couldn't experience whole hotel but would stay there again.
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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