
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.


Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
This was my first time staying. The staff was very friendly and helpful. Our room was very nice and perfectly located downtown. Also, the breakfast buffet was amazing and a nice surprise.
Reviewed on 9 Aug 2025



Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
I liked this hotel, the rooms are cleaning and beautiful, the staff is nice, and the hotel is located near amazing restaurants, cafes, and tourist places.
Reviewed on 9 Aug 2025
Top hotels in Chesterton

Spring House Inn
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is €109 per night from 2 Sept to 3 Sept
€109
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Friendly staff. Clean room. Drapes made the room dark and nice for sleeping in! Nice breakfast choices. Pool was closed for maintenance for part of one day, but fixed in a very timely manner to open by that evening. Staff addressed any concerns we had (one key card didn’t work and one wouldn’t open ..."
Reviewed on 8 Aug 2025

Best Western Indian Oak
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is €98 per night from 1 Sept to 2 Sept
€98
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"Loved the lake"
Reviewed on 7 Aug 2025

Waterbird Lakeside Inn
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
8/10 Very Good! (899 reviews)
"Nice and clean place to stay!"
Reviewed on 7 Aug 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.
Frequently asked questions
More trip options
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.