Chesterton Holidays
Photo by City Circus Wandering
- Plan, book, travel with confidence
Better together
Save up to €185 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 Flight + Hotel Deals in Chesterton
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Price was €1,083, price is now €844 per person
€844
per person
2 Nov - 7 Nov
found 8 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (3,910 reviews)
Property directly in downtown.. very busy and nosiey. View of city is obstructed by other tall buildings. Parking is high and not convenient.
Reviewed on 29 Sept 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,527, price is now €1,090 per person
€1,090
per person
31 Oct - 3 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Perfect location, beautiful view, nice staffs, excellently maintained room and facility!
Reviewed on 28 Sept 2025
Park Hyatt Chicago
Downtown Chicago
Price was €2,271, price is now €1,724 per person
€1,724
per person
2 Nov - 7 Nov
found 8 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Fantastic stay with excellent staff ! Would 100% recommend and will be returning the next time we are in Chicago.
Reviewed on 27 Sept 2025
Top hotels in Chesterton
Best Western Indian Oak
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is €98 per night from 8 Oct to 9 Oct
€98
8 Oct - 9 Oct
includes taxes & fees
8.4/10 Very Good! (1,017 reviews)
"all"
Reviewed on 28 Sept 2025
Waterbird Lakeside Inn
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
8/10 Very Good! (952 reviews)
"Very tranquil."
Reviewed on 27 Sept 2025
Spring House Inn
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is €99 per night from 5 Oct to 6 Oct
€99
5 Oct - 6 Oct
includes taxes & fees
8.8/10 Excellent! (1,033 reviews)
"The main areas inside are really nice and there are seating areas outside. It's in a beautiful wooded area and super close to the national park. Our room had a smell like urine and stale cigarette smoke, but we would consider staying again."
Reviewed on 27 Sept 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.
More trip options
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
