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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$604

The Champagne Lodge & Luxury Suites

16 W 621 S. Frontage Rd, Willowbrook - Map
 
 
"5 star"
Great .. I love the room and the room service was great to!!
A Traveller
dana hotel and spa - Chicago Hotels
Rating: 4.0 Stars
C$291

dana hotel and spa

660 North State Street, Chicago - Map
 
 
"Trendy and stylish"
My husband and I live in the city and were looking for a short baby moon get away before our second child arrived. We usually stay at the Peninsula or Langham but wanted to try something with a different feel. We had heard great things about the Dana and had walked by it several times. When we arrived we were instantly greeted by the bell hop who was so kind and very personable. The concierge was also friendly and prompt. The style of the hotel we loved, from the concrete ceiling to the industrial feel of exposed beams and rustic floor. We had the corner king and the windows were spectacular. The styling of the room was modern but the colors made it feel warm. The shower and bathroom was also very intriguing and modern. I loved the barn door to the bathroom that also hid the closet when the door was open. It was a great Chicago view and in the middle of the night it was a sparkling concrete jungle to behold. Surprisingly enough the windows were very sound proof and we never heard the busy sounds of the city or our hotel neighbors. Definitely will be going back.
Kyla from Chicago, IL
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$517

The Peninsula Chicago

108 East Superior Street, Chicago - Map
 
 
The best hotel in Chicago! Great location to shops, restaurants and museums. Very safe and friendly. The hotel's staff are the best in Chicago and the rooms are perfect.
A Traveller
The James Chicago - Chicago Hotels
Rating: 4.5 Stars

The James Chicago

55 East Ontario Street, Chicago - Map
 
 
"Friendly staff, close to all"
This is the only hotel I stay in when I travel to Chicago. Great staff, very friendly and accommodating. The bed is very comfy and bathroom products are amazing! DB Primehouse is my favorite steak house; however the hotel bar and Jimmy next door are dead. The location is central and close to all...you won't be disappointed!
Sheila from new york, ny
The Drake Hotel - Chicago Hotels
Rating: 4.0 Stars

The Drake Hotel

140 E Walton Place, Chicago - Map
 
 
"Perfect location!"
The location of this hotel is perfect for dining and shopping. It is easy to access both airports, as well. We stayed for a professional meeting, met friends here driving in from Michigan, and celebrated our anniversary. The florist downstairs did a beautiful job with the arrangement sent to the room.
V from SC
Sofitel Chicago Water Tower - Chicago Hotels
Rating: 4.5 Stars

Sofitel Chicago Water Tower

20 E Chestnut St, Chicago - Map
 
 
"Good business hotel"
Was there all week and very comfortable. Great location, comfortable bed, clean, good restaurant.
Joe from NY, NY
Waldorf Astoria Chicago - Chicago Hotels
Rating: 5.0 Stars

Waldorf Astoria Chicago

11 E. Walton Street, Chicago - Map
 
 
"Stressful trip made special"
Our recent trip to Chicago was for University auditions and interviews. Needless to say it was a hectic and stressful time. Travelling with my two daughters aged 18 years and under 2 also added to the challenge of finding a spot that was both comfortable and functional. The Waldorf Astoria Chicago was everything and more. The fitness centre was bright cheerful and fully equipped to satisfy my older daughter and my work out needs and the pool was a special place to share time with my toddler. The restaurant staff were always helpful and attentive, keeping the pace moving so there were no melt downs or disturbances to other patrons. The Doormen were most helpful in obtaining vehicles as needed and assisted with the loading of a tricky stroller always with a smile. The housekeeping staff had a keen sense of how many towels and toilet articles to leave from the first day and the complimentary turn down service was a real treat. Our trip to Chicago could not have been better thanks to all the staff at the Waldorf. I will look forward to staying there again in the future.
Robbie from Toronto, Ontario Canada
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$299

The Whitehall Hotel

105 E Delaware Pl, Chicago - Map
 
 
"Classy historic hotel"
I really enjoyed my two nights at the Whitehall. It's a classic, historic building, but with rooms that are more or less up-to-date in terms of decoration. It was also very clean, and had great beds. Overall, it's a great place to stay!
David from Canada
Hotel Monaco Chicago, a Kimpton Hotel - Chicago Hotels
Rating: 4.0 Stars

Hotel Monaco Chicago, a Kimpton Hotel

225 N Wabash Ave, Chicago - Map
 
 
"Perfect location, great service"
Close to Chicago's most important attractions like the millennium park, museum of art, and Michigan Ave. Complimentary wine hour everyday, and compliantaty coffee and tea every morning. Elegant decor, and friendly staff. Would definitely recommend it and stay in it again.
Zain from Royal Oak, MI
Hotel Chicago Downtown, Autograph Collection - Chicago Hotels
Rating: 4.0 Stars

Hotel Chicago Downtown, Autograph Collection

333 N Dearborn St, Chicago - Map
 
 
"Awesome"
Awesome location with lots of excellent restaurants, bars and stores in a walking distance Very clean and spacious room (At least for a couple) with big bathroom Lobby was in remodelation but didn't bothered us at all No Free WiFi
Michel from Miami

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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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    91% recommended
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    From 29,939 Reviews