Central Chicago Honeymoon Vacations
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Flight and Honeymoon hotel deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $913, price is now CA $671 per person
CA $671
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.
Reviewed on Nov 3, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was CA $1,352, price is now CA $941 per person
CA $941
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips5* Honeymoon holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,540, price is now CA $1,943 per person
CA $1,943
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful
Reviewed on Nov 10, 2026
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips3 Night Honeymoon holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was CA $1,352, price is now CA $941 per person
CA $941
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips4 Night Honeymoon holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,540, price is now CA $1,943 per person
CA $1,943
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful
Reviewed on Nov 10, 2026
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all tripsThings to do
Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $57
per adult
94% of travellers recommend
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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.
