West Side Honeymoon Vacations
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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 7 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
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,773, price is now CA $1,259 per person
CA $1,259
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!
Reviewed on Feb 19, 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 21 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.
Level Chicago – Old Town
Downtown Chicago
Price was CA $951, price is now CA $717 per person
CA $717
per person
Mar 26 - Mar 29
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!
Reviewed on Feb 19, 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 10 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 7 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
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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.
