Chicago Honeymoon Vacations
Book a Honeymoon Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ￥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Honeymoon vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
per person
Sep 21 - Sep 24
just found
Roundtrip non-stop flight included
Singapore (SIN) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
Hilton Chicago O'Hare Airport
O'Hare
per person
Sep 21 - Sep 25
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.2/10 Very Good! (2,055 reviews)
Hotel is just ok but we were delayed all day on a flight got in at 1:00am and obviously missed our connection. So we had about 5 hours before catching a new flight the next morning and you can literally walk to and from the hotel to the departure area in 5 mins. Staff was very friendly and helpful.
Reviewed on Jul 17, 2025
5* Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
per person
Sep 21 - Sep 24
just found
Roundtrip non-stop flight included
Singapore (SIN) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
3 Night Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
per person
Sep 21 - Sep 24
just found
Roundtrip non-stop flight included
Singapore (SIN) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everything about this hotel is on point. The staff is professional and gracious. The property is extremely well maintained. They leave no detail of your comfort unaddressed.
Reviewed on Jul 15, 2025
4 Night Honeymoon vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Top Honeymoon Chicago Hotels
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Stay at this 4-star 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 ...
8.8/10 Excellent! (3,044 reviews)
"Great"
Reviewed on Jul 18, 2025
The Wade
644 N Lake Shore Dr, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy room service, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff ...
8.2/10 Very Good! (1,103 reviews)
"Good hotel to see he fireworks and to walk to Navy Pier."
Reviewed on Jul 17, 2025
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)
"It was a great hotel but their parking was awfully far from my room"
Reviewed on Jul 17, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.