Illinois Honeymoon Vacations
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Flight and Honeymoon hotel deals in Illinois
Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel
Downtown Chicago
Price was CA $980, price is now CA $781 per person
CA $781
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,993 reviews)
The room was incredibly clean and had a great view! The staff was so nice and Deandre was such a wonderful host at checkout. Thank you for the amazing stay!
Reviewed on Jan 29, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,401, price is now CA $1,033 per person
CA $1,033
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,008, price is now CA $811 per person
CA $811
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $1,480, price is now CA $1,202 per person
CA $1,202
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,024, price is now CA $836 per person
CA $836
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The staff is incredible. We always enjoy staying here!
Reviewed on Feb 8, 2026
5* Honeymoon holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,401, price is now CA $1,033 per person
CA $1,033
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 CA $1,480, price is now CA $1,202 per person
CA $1,202
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 Langham, Chicago
Downtown Chicago
Price was CA $1,909, price is now CA $1,591 per person
CA $1,591
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Gorgeous property, facilities, and location.
Reviewed on Feb 6, 2026
3 Night Honeymoon holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,008, price is now CA $811 per person
CA $811
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $1,835, price is now CA $1,247 per person
CA $1,247
per person
Apr 3 - Apr 6
found 16 hours ago
Roundtrip flight included
Calgary (YYC) 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,944, price is now CA $1,430 per person
CA $1,430
per person
Mar 13 - Mar 16
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
4 Night Honeymoon holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel
Downtown Chicago
Price was CA $980, price is now CA $781 per person
CA $781
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,993 reviews)
The room was incredibly clean and had a great view! The staff was so nice and Deandre was such a wonderful host at checkout. Thank you for the amazing stay!
Reviewed on Jan 29, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,919, price is now CA $1,437 per person
CA $1,437
per person
Mar 12 - Mar 16
just found
Roundtrip flight included
Toronto (YYZ) 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
Honeymoon Hotels in Illinois
Eurostars Magnificent Mile
660 North State Street Chicago IL
The price is CA $131 per night from Feb 22 to Feb 23
CA $131
CA $154 total
Feb 22 - Feb 23
includes taxes & fees
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! (3,214 reviews)
The staff was very nice. Hotel is located in a good spot so walking or the bus was sufficient. Very helpful and considerate. I would stay here again if I ever return to this city.
Reviewed on Feb 7, 2026
The Wade
644 N Lake Shore Dr Chicago IL
The price is CA $122 per night from Feb 12 to Feb 13
CA $122
CA $143 total
Feb 12 - Feb 13
includes taxes & fees
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! (1,652 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
The price is CA $208 per night from Feb 18 to Feb 19
CA $208
CA $227 total
Feb 18 - Feb 19
includes taxes & fees
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
