Chicago Honeymoon Vacations
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Flight and Honeymoon hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,113, price is now CA $904 per person
CA $904
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Staff was very good, attentive. The property itself is in a great location, but the room showed some wear and tear - exposed drywall screws holding on bathroom door trim with some paint slapped on it, smelly sink, water damage and peeling paint on inside window sill, visually boring interior that looks like it's from the 1990's
Reviewed on May 12, 2026
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,591, price is now CA $1,229 per person
CA $1,229
per person
Jul 23 - Jul 26
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (1,091 reviews)
I would have really appreciated if there were a microwave available in our room.
Reviewed on May 4, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,182, price is now CA $954 per person
CA $954
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy.
My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand many hotels are moving in this direction, but travelers should be aware of the additional required cost when budgeting for their stay. Outside of that, the team and location were the highlights for me.
Reviewed on May 12, 2026
Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
Price was CA $1,700, price is now CA $1,382 per person
CA $1,382
per person
Jun 19 - Jun 23
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,522 reviews)
Bar and bar manager was very helpful and great young man… Nest part of the stay !
Reviewed on May 12, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $2,504, price is now CA $2,039 per person
CA $2,039
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The morning coffee was excellent. We asked about tea in the evening and akettle and wonderful teas were brought to our room. We went to the bar for happy hour and the appetizers were great as were the prices. Nice location. Friendly staff.
Reviewed on May 12, 2026
5* Honeymoon holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,911, price is now CA $1,610 per person
CA $1,610
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I LOVE THIS HOTEL!!!
Reviewed on May 13, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $2,784, price is now CA $2,394 per person
CA $2,394
per person
Jun 13 - Jun 16
just found
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Loved the location. Loved the property , staff, amenities, and service. I did not live the brutal Chicago cold. Four below is just hateful cold weather. Want to return this summer or fall to enjoy the area. Excellent property. Definitely recommend you stay if in Chicago.
Reviewed on May 10, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,776, price is now CA $3,359 per person
CA $3,359
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
I truly enjoyed my 5 night stay at this hotel. Everyone was helpful, friendly, and accommodating. I love its location, near the Michael mile.
When I return to Chicago I will definitely stay at the Park Hyatt.
Reviewed on Apr 4, 2026
3 Night Honeymoon holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,813, price is now CA $1,304 per person
CA $1,304
per person
Jul 23 - Jul 26
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,122 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
4 Night Honeymoon holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,689, price is now CA $1,249 per person
CA $1,249
per person
Jun 12 - Jun 16
just found
Roundtrip non-stop flight included
Minot (MOT) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy.
My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand many hotels are moving in this direction, but travelers should be aware of the additional required cost when budgeting for their stay. Outside of that, the team and location were the highlights for me.
Reviewed on May 12, 2026
Honeymoon Hotels in Chicago
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 ...
9/10 Wonderful! (3,522 reviews)
The staff was nice. The property was a little outdated. The air conditioner in the room was terribly loud and made it very difficult to get any sleep. I checked out and went to leave and my vehicle had been blocked in by the valet for the restaurant in the hotel. I would’ve had no way to figure it ...
Reviewed on May 12, 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! (1,827 reviews)
No good cell signal but overall a good stay
Reviewed on May 11, 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. ...
9/10 Wonderful! (1,016 reviews)
5 stars
Reviewed on May 10, 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.
