Chicago Romantic Holidays
Book a Romantic Hotel + Flight or Car together to unlock savings
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Save up to ₹43,962 when you book a flight and hotel together*
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Top flight + Romantic hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025
5* Romantic holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025
Top Romantic Chicago Hotels
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd, Willowbrook, IL
Stay at this 3.5-star boutique hotel in Willowbrook. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,142 reviews)
Couples like: adults-only property, hot tub, fireplace, romance packages available
Travellers say...
"Nice property"
Reviewed on 1 Jul 2025
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the bar and the helpful staff in their ...
9.2/10 Wonderful! (3,341 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travellers say...
"Great stay"
Reviewed on 3 Jul 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge) and a 24-hour health club. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,772 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travellers say...
"beautiful hotel, friendly and helpful staff."
Reviewed on 2 Jul 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.
More Holiday Ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.