Chicago Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Romantic vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ￥367,952, price is now ￥293,702 per person
￥293,702
per person
Apr 30 - May 6
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Staff was excellent and the building is literally iconic. Our only negative is that the bathrooms were a bit tired. Ours had a yellowed, loose fitting toilet seat and a light out on the mirror.
Reviewed on Feb 2, 2026
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥579,324, price is now ￥388,004 per person
￥388,004
per person
Apr 30 - May 6
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Pendry Chicago
Downtown Chicago
Price was ￥478,193, price is now ￥332,532 per person
￥332,532
per person
Apr 30 - May 6
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026
5* Romantic vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥389,597, price is now ￥332,506 per person
￥332,506
per person
Apr 17 - Apr 21
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥579,324, price is now ￥388,004 per person
￥388,004
per person
Apr 30 - May 6
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
3 Night Romantic vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥297,018, price is now ￥274,782 per person
￥274,782
per person
May 2 - May 4
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.
Reviewed on Feb 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥370,676, price is now ￥324,472 per person
￥324,472
per person
Mar 27 - Mar 29
found 18 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
The Godfrey Hotel Chicago
Downtown Chicago
Price was ￥317,044, price is now ￥292,652 per person
￥292,652
per person
May 2 - May 4
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,887 reviews)
The was clean the halls was clean the front desk check in staff was quick with check in and very nice
Reviewed on Feb 6, 2026
4 Night Romantic vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Chicago
Downtown Chicago
Price was ￥271,912, price is now ￥239,802 per person
￥239,802
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Staff was super friendly and rooms were clean. Definitely will come back
Reviewed on Jan 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥389,597, price is now ￥332,506 per person
￥332,506
per person
Apr 17 - Apr 21
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥310,704, price is now ￥269,584 per person
￥269,584
per person
Apr 17 - Apr 21
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Nice room and friendly staff. Bar and restaurant were both great as well
Reviewed on Feb 6, 2026
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! (1,390 reviews)
Couples like: adults only property, spa tub, fireplace, romance packages available
Travelers say...
Everything was outstanding
Reviewed on Feb 3, 2026
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! (3,587 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
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
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
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.
