Chicago Romantic Vacations
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Top Romantic vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
per person
Sep 21 - Sep 24
found 8 hours ago
Roundtrip non-stop flight included
Singapore (SIN) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
5* Romantic vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
per person
Sep 21 - Sep 24
found 8 hours ago
Roundtrip non-stop flight included
Singapore (SIN) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
3 Night Romantic vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
4 Night Romantic vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Top Romantic Chicago Hotels
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd, Willowbrook, IL
For a romantic stay, consider this boutique hotel, featuring a garden, jetted tubs, and in-room fireplaces. Couples will appreciate the romance packages and ...
8.4/10 Very Good! (1,167 reviews)
Couples like: adults only property, spa tub, fireplace, romance packages available
Travelers say...
"Enjoyed my stay will be returning"
Reviewed on Jul 17, 2025
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive, Chicago, IL
Indulge in a romantic getaway at this upscale hotel, where you'll find a spa, in-room massages, and onsite dining. Couples will love the Frette Italian sheets ...
9.4/10 Exceptional! (3,335 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travelers say...
"The location of the hotel was perfect. A lot of restaurants and tourist attractions were walking distance and majority of the public transportation was near by as well"
Reviewed on Jul 19, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Fall in love again at this historic hotel. You and your special someone are sure to love the spa, premium mattresses, and luxury bedding. You'll also appreciate ...
8.2/10 Very Good! (1,784 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travelers say...
"Beautiful historic hotel! Loved the live music in the lobby. I was there in a traditional room sith 2 double beds, and then i upgraded to a suite. Both were nice rooms, but i LOVE a good suite! Personnel at the hotel were kind and helpful. Have a cocktail and a brownie in the lobby- you won't regret ..."
Reviewed on Jul 15, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.