Chicago Honeymoon Holidays
Book a Honeymoon Hotel + Flight or Car together to unlock savings
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Save up to £335 when you book a flight and hotel together*
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With over 300,000 hotels worldwide, it's easy to create a perfect package
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Packages with flights are ATOL protected
Top flight + Honeymoon hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
3 Sept - 6 Sept
found 4 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 12 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
I had such a lovely staycation, and I recommend a stay here to everyone I know.
Reviewed on 26 Jun 2025
Hilton Chicago O'Hare Airport
O'Hare
per person
11 Sept - 16 Sept
found 2 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.2/10 Very Good! (2,069 reviews)
Item was left in room. I tried for days to get contact with front desk and security will little to no luck. They say nothing reported so I consider that as theft by staff. Very disappointing.
Reviewed on 2 Jul 2025
5* Honeymoon holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
3 Sept - 6 Sept
found 4 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025
3 Night Honeymoon holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
13 Aug - 16 Aug
found 2 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025
4 Night Honeymoon holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
4 Aug - 8 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025
Top Honeymoon Chicago Hotels
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Stay at this 4-star spa hotel in Chicago. Enjoy free Wi-Fi, a full-service spa and a fitness centre. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (3,019 reviews)
Great service, great location, no rooftop
"The hotel is beautiful, in a great location with amazing staff. Unfortunately, the rooftop was not available which was a major reason for booking this hotel. Overall, it is a nice hotel."
Reviewed on 1 Jul 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 centre and valet parking (surcharge). Our guests praise the helpful staff ...
8.2/10 Very Good! (1,041 reviews)
"I haven't been to the property since it was the W hotel and it was a nice change. Frank at the front desk was AMAZING and made our check in experience effortless. My only issue was the bedand pillows were uncomfortable and the hotel was a bit warm. Our suite had two tv sets but there was only one ..."
Reviewed on 1 Jul 2025
Hyatt Lodge Oak Brook Chicago
2815 Jorie Blvd, Oak Brook, IL
Stay at this spa hotel in Oak Brook. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
8.6/10 Excellent! (1,005 reviews)
"Excellent customer service"
Reviewed on 1 Jul 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.
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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. Flight-inclusive packages are ATOL protected.