Best Romantic Hotels in Chicago IL

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Ivy Boutique Hotel
Hotel in Chicago IL

Excellent 9

241 reviews

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Romantic Hotel

Guests can enjoy the tranquil setting of our rooftop bar the Sky Terrace during the summer months, the small plates and signature cocktails delivered to their suite, or visit DiVine Lounge open year-round.

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Hampton Inn & Suites Chicago-Downtown
Hotel in Chicago IL

Very Good 8.7

808 reviews

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A great value hotel in downtown Chicago. Each one of the 230 guest rooms and suites offers a sumptuous bed, free WiFi and a 37-inch TV.

Romantic Hotel

Hotel with Swimming Pool

The hotel features a year-round indoor swimming pool. Indoor Pool

Hotel for Honeymoon

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Staypineapple, The Loop
Hotel in Chicago IL

Excellent 9.2

993 reviews

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Have an unforgettable romantic stay at a National Historic Landmark building that was built in 1895 and it was considered one of the city's first skyscrapers!

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The Silversmith Hotel
Hotel in Chicago IL

Excellent 9.1

609 reviews

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The hotel features a "Chicago Romantic Getaway" package that includes luxurious accommodations, breakfast in bed, a map of jeweler row and a bottle of champagne and amenity in room upon arrival.

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Hotel Blake, an Ascend Hotel Collection Member
Hotel in Chicago IL

Excellent 8.8

322 reviews

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Romantic Hotel

Boutique Hotel

Luxury Hotel

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Holiday Inn Hotel & Suites Chicago - Downtown
Hotel in Chicago IL

Good 7.9

267 reviews

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Romantic Hotel

Hotel for Honeymoon

Family Friendly Hotel

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Embassy Suites Chicago - Downtown
Hotel in Chicago IL

Very Good 8.6

976 reviews

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Romantic Hotel

Luxury Hotel

Hotel for Honeymoon

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Cambria Hotel Chicago Magnificent Mile
Hotel in Chicago IL

Excellent 8.9

1120 reviews

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The over-sized guest rooms and suites styled with a splash of Chicago flair, showcase dreamy views which will ignite a romance with this extraordinary city.

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The Blackstone, Autograph Collection
Hotel in Chicago IL

Excellent 8.9

70 reviews

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Renaissance Blackstone features a unique setting that will make your stay both extraordinary and memorable. Nothing can surpass the hotel's rich classical architecture, beautifully combined with contemporary accents.

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River Hotel
Hotel in Chicago IL

Very Good 8.5

2026 reviews

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Romantic Hotel

Boutique Hotel

Hotel for Honeymoon

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Ruby Room
Chicago IL

Very Good 8

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Romantic Accommodation

Historic Accommodation

Accommodation near Bars And Clubs

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Corporate Suites in the Heart of Magnificent Mile
Apartments in Chicago IL

Very Good 8.3

231 reviews

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Romantic Accommodation

Luxury Accommodation

Family Friendly Accommodation

Marriott Marquis Chicago
Hotel in Chicago IL

Excellent 8.8

304 reviews

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Romantic Hotel

Hotel for Honeymoon

Hotel with Parking

Corporate Suites Network 73 East Lake
Apartment in Chicago IL

Excellent 9.7

22 reviews

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Romantic Accommodation

Accommodation with Spa

Accommodation with Swimming Pool

Heated Pool Indoor Pool

East Bowen Avenue Apartment
Apartment in Chicago IL

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Romantic Accommodation

Family Friendly Accommodation

Small Accommodation

*Prices above are average nightly rates as provided by our partners for one room, double occupancy and might not include all taxes and fees. Please see our booking partners websites for full details.