Chicago Honeymoon Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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
Flight and Honeymoon hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $856, price is now CA $630 per person
CA $630
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9/10 Wonderful! (2,484 reviews)
Staff was friendly, however I asked to have blankets brought up to room two times (one phone call and one text) and there was no follow through. The room smelled like stale smoke. The pull out bed was awful and you could feels the bedsprings. They also offered to bring coffee to the room and when I requested a time, it was never delivered. I mentioned to from desk and they apologized and had coffee sent to room, however we were ready to check out. They did offer a late check out and staff was friendly. We were dissapointed that we couldn't pay cash, although that wouldn't have been a deal breaker. Rooms could use a little updating.
Reviewed on Apr 4, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,177, price is now CA $829 per person
CA $829
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
The hotel itself is beautiful, the lounge and bar area are so cozy and the cocktails are amazing! The entire staff is friendly and welcoming. Our stay at The Pendry was great! Shout out to our friend Anis at the bar lounge for his excellent hospitality.
Reviewed on Apr 4, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,782, price is now CA $1,966 per person
CA $1,966
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 2026
Hotel 55 Chicago Downtown
Downtown Chicago
Price was CA $1,436, price is now CA $1,076 per person
CA $1,076
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,575 reviews)
The room was spacious and the decor was lovely. It was conveniently located right next to Marshalls, making it easy to grab a quick snack or a new pair of shoes. The hotel is also just a 10-minute walk from the riverfront, where you can enjoy a leisurely stroll or take a boat ride. From there, it’s only a 5-6 minute walk to the Bean, a popular coffee shop that’s perfect for a quick caffeine fix. And if you’re looking for some shopping, the Starbucks Reserve is just a 2-minute walk away. Overall, this hotel offers a great combination of convenience and amenities, making it a perfect choice for any traveler.
Reviewed on Apr 4, 2026
5* Honeymoon holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,782, price is now CA $1,966 per person
CA $1,966
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,882, price is now CA $1,425 per person
CA $1,425
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Highly recommend a stay here! The staff are amazing and the restaurant is incredible; get the French toast.
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 $1,177, price is now CA $829 per person
CA $829
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
The hotel itself is beautiful, the lounge and bar area are so cozy and the cocktails are amazing! The entire staff is friendly and welcoming. Our stay at The Pendry was great! Shout out to our friend Anis at the bar lounge for his excellent hospitality.
Reviewed on Apr 4, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,782, price is now CA $1,966 per person
CA $1,966
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 2026
4 Night Honeymoon holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $3,600, price is now CA $2,509 per person
CA $2,509
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $2,041, price is now CA $1,554 per person
CA $1,554
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
A quiet and comfortable place
Reviewed on Apr 4, 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! (3,374 reviews)
Phenomenal nothing else to say top notch
Reviewed on Apr 5, 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! (1,774 reviews)
Clean room, great view, close to lake! Loved!
Reviewed on Apr 3, 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! (1,003 reviews)
Unhappy about the hot tub. It had a weird film present on top within the bubbles. Looked like dirt, or grime. Room was pretty clean, some minor noted stains on curtains. The carpeting was recently replaced which I had a big problem with and left reviews on it our last visit here. It really is a great ...
Reviewed on Apr 4, 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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
