
Chesterton Holidays
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Top Flight + Hotel Deals in Chesterton
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Very friendly staff, hotel needs renovation. Pool dated some stones missing by pool & ceiling needs painting.
Reviewed on 4 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,342 reviews)
London house did not disappoint. View room was a highlight, staff were friendly and courteous. Close walk to Riverwalk, tours, parks, museums and shops. Make reservations for LH rooftop. I only wish I was able to get credit with Hilton for the stay.
Reviewed on 3 Aug 2025


Level Chicago - River North
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).
Reviewed on 27 Jul 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 €110 per night from 2 Sept to 3 Sept
€110
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"We enjoyed staying at the Spring House Inn! The room was clean and spacious. There were great options at the continental breakfast. The staff was friendly & helpful! Our stay was great!"
Reviewed on 30 Jul 2025

Best Western Indian Oak
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is €99 per night from 1 Sept to 2 Sept
€99
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
It was fine. Probably wouldn’t choose it again.
"This hotel was ok. Not the worst I’ve stayed at and not the best. Front desk seemed frazzled. While the room was mostly clean, there were cigarette butts left on the patio. It was walking distance to several eateries which was helpful."
Reviewed on 28 Jul 2025

Waterbird Lakeside Inn
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
8/10 Very Good! (896 reviews)
"Nice quiet area"
Reviewed on 1 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.
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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.