Chicago Honeymoon Vacations
Book a Honeymoon Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 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
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Top Honeymoon vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Downtown Chicago
Price was ₩2,795,260, price is now ₩2,538,070 per person
₩2,538,070
per person
May 29 - Jun 1
found 9 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.6/10 Exceptional! (1,212 reviews)
Property is a building with classical bones. But, super pleasant and super peaceful!
Reviewed on Mar 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ₩3,825,674, price is now ₩2,936,126 per person
₩2,936,126
per person
May 29 - Jun 1
found 9 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ₩3,371,724, price is now ₩2,602,647 per person
₩2,602,647
per person
May 29 - Jun 1
found 9 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Clean room nice staff, beautiful property. Enjoyed the deluxe room
Reviewed on Mar 20, 2026
The Godfrey Hotel Chicago
Downtown Chicago
Price was ₩3,356,098, price is now ₩2,935,402 per person
₩2,935,402
per person
May 29 - Jun 1
found 9 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Clean room , lovely staff and great location
Reviewed on Mar 19, 2026
The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
Price was ₩3,098,004, price is now ₩2,807,032 per person
₩2,807,032
per person
May 29 - Jun 1
found 9 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
7.6/10 Good! (1,227 reviews)
Still waiting on refund
Reviewed on Mar 18, 2026
5* Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ₩3,825,674, price is now ₩2,936,126 per person
₩2,936,126
per person
May 29 - Jun 1
found 9 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026
3 Night Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
Price was ₩3,371,724, price is now ₩2,602,647 per person
₩2,602,647
per person
May 29 - Jun 1
found 9 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Clean room nice staff, beautiful property. Enjoyed the deluxe room
Reviewed on Mar 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ₩3,825,674, price is now ₩2,936,126 per person
₩2,936,126
per person
May 29 - Jun 1
found 9 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026
The Godfrey Hotel Chicago
Downtown Chicago
Price was ₩3,356,098, price is now ₩2,935,402 per person
₩2,935,402
per person
May 29 - Jun 1
found 9 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Clean room , lovely staff and great location
Reviewed on Mar 19, 2026
Top Honeymoon Chicago Hotels
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! (3,317 reviews)
Clean room nice staff, beautiful property. Enjoyed the deluxe room
Reviewed on Mar 20, 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! (1,744 reviews)
My experience at the Wade Hotel was very disappointing. First, I didn’t receive the room I originally requested. When I was moved to another room, it turned out to be even worse, so I had to return to the first one. The cleanliness was a major issue, the rooms were dirty and not well-maintained. ...
Reviewed on Mar 21, 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! (1,002 reviews)
my wife and I had an amazing stay here the staff and rooms were great! only reason why i gave 4 stars not 5 is that we had requested through the booking to have a crib and a lake facing room to which the facility did not reply but the crib was supplied once we got there and asked, but overall great ...
Reviewed on Mar 18, 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.
