Chicago Honeymoon Vacations
Book a Honeymoon 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 Honeymoon vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥79,328, price is now ￥67,976 per person
￥67,976
per person
Mar 16 - Mar 18
found 16 hours ago
Roundtrip flight included
Omaha (OMA) 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 ￥141,213, price is now ￥103,835 per person
￥103,835
per person
Mar 16 - Mar 18
found 16 hours ago
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥609,021, price is now ￥481,736 per person
￥481,736
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) 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 ￥96,488, price is now ￥80,597 per person
￥80,597
per person
Mar 16 - Mar 18
found 16 hours ago
Roundtrip flight included
Omaha (OMA) 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
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥115,928, price is now ￥97,924 per person
￥97,924
per person
Mar 16 - Mar 18
found 16 hours ago
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Easy booking, they let me check in early which I needed it. Friendly staff, nice bed, good shower pressure, clean room. Just need some updating to make it brighter room. Overall satisfied with my stay.
Reviewed on Feb 2, 2026
5* Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥141,213, price is now ￥103,835 per person
￥103,835
per person
Mar 16 - Mar 18
found 16 hours ago
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥609,021, price is now ￥481,736 per person
￥481,736
per person
Mar 16 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) 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
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥304,308, price is now ￥245,655 per person
￥245,655
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff and amenities
Reviewed on Feb 4, 2026
3 Night Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was ￥235,598, price is now ￥198,214 per person
￥198,214
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥286,713, price is now ￥240,126 per person
￥240,126
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥301,802, price is now ￥255,608 per person
￥255,608
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) 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
4 Night Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥322,052, price is now ￥289,640 per person
￥289,640
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Easy booking, they let me check in early which I needed it. Friendly staff, nice bed, good shower pressure, clean room. Just need some updating to make it brighter room. Overall satisfied with my stay.
Reviewed on Feb 2, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥510,170, price is now ￥440,616 per person
￥440,616
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Friendly staff, accommodating- we arrived earlier than our check-in time and they were able to get us in our room promptly.
Reviewed on Feb 3, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥437,054, price is now ￥389,742 per person
￥389,742
per person
May 1 - May 5
found 1 day ago
Roundtrip 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
Top Honeymoon Chicago Hotels
Eurostars Magnificent Mile
660 North State Street Chicago IL
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (3,208 reviews)
Great rooms and easy check in. Can’t believe I haven’t stayed here before. I’ll be be back!
Reviewed on Feb 4, 2026
The Wade
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,647 reviews)
Room was nice a little dated but I still enjoyed the room it was really clean room service was nice. Pool was nice and empty
Reviewed on Jan 31, 2026
Hyatt Lodge Oak Brook Chicago
2815 Jorie Blvd Oak Brook IL
Book a stay at this spa hotel in Oak Brook. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,006 reviews)
Staff were all warm and welcoming. The pool/spa area was gorgeous and clean.
Reviewed on Feb 3, 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.
