Chicago Romantic Vacations

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    Save up to ¥45,448 when you book a flight and hotel together*
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Top Romantic vacation packages in Chicago

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Staypineapple, An Iconic Hotel, The Loop
Waldorf Astoria Chicago
Pendry Chicago
The Peninsula Chicago
L7 Chicago by LOTTE
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5* Romantic vacations in Chicago

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Trump International Hotel & Tower Chicago
Waldorf Astoria Chicago
The Peninsula Chicago
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3 Night Romantic vacations in Chicago

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Hotel Felix River North/Magnificent Mile
Trump International Hotel & Tower Chicago
The Godfrey Hotel Chicago
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4 Night Romantic vacations in Chicago

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Virgin Hotels Chicago
Trump International Hotel & Tower Chicago
LondonHouse Chicago, Curio Collection by Hilton
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Top Romantic Chicago Hotels

The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
  • 44 min drive from Wrigley Field
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! (1,390 reviews)

Couples like: adults only property, spa tub, fireplace, romance packages available

Travelers say...
Everything was outstanding

Reviewed on Feb 3, 2026

The Champagne Lodge & Luxury Suites
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive Chicago IL
  • 10 min drive from Wrigley Field
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! (3,587 reviews)

Couples like: full-service spa, couples spa treatments, bar

Travelers say...
Nice room and friendly staff. Bar and restaurant were both great as well

Reviewed on Feb 6, 2026

LondonHouse Chicago, Curio Collection by Hilton
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
  • 12 min drive from Wrigley Field
You and your special someone are sure to love the
8.4/10 Very Good! (2,278 reviews)

Couples like: full-service spa, couples spa treatments, happy hour

Travelers say...
Hotel and staff was great. Great location. Just wish more elevators worked because it was a huge audition festival and elevator situation was dire.

Reviewed on Feb 6, 2026

Palmer House a Hilton Hotel
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.