West Side Honeymoon Vacations
Book a Hotel + Flight or Car together to unlock savings
Photo by throwingsofas
- 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 West Side
Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
Price was CA $1,208, price is now CA $772 per person
CA $772
per person
Apr 24 - Apr 28
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,919, price is now CA $1,141 per person
CA $1,141
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026
JW Marriott Chicago
Downtown Chicago
Price was CA $1,455, price is now CA $980 per person
CA $980
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again .
Reviewed on Feb 17, 2026
5* Honeymoon holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,238, price is now CA $1,796 per person
CA $1,796
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great hotel, plus excellent service me and my wife like it we definitely coming back thanks
Reviewed on Feb 17, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,586, price is now CA $2,099 per person
CA $2,099
per person
May 17 - May 21
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The staff were lovely. As it was our anniversary, we were given a beautiful room overlooking the water tower and the lake. The room was exceptional - the bath tub, huge! The hotel itself was within walking distance to almost everywhere - the lake, the river, the magnificent mile. There were cafes and restaurants very close by. We had a fantastic time in Chicago because of this!
Reviewed on Feb 20, 2026
3 Night Honeymoon holidays in West Side
Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,465, price is now CA $918 per person
CA $918
per person
Apr 30 - May 3
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again .
Reviewed on Feb 17, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,149, price is now CA $815 per person
CA $815
per person
Mar 26 - Mar 29
found 12 hours ago
Roundtrip flight included
Toronto (YTO) 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
4 Night Honeymoon holidays in West Side
Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
Price was CA $1,208, price is now CA $772 per person
CA $772
per person
Apr 24 - Apr 28
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,919, price is now CA $1,141 per person
CA $1,141
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026
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.
