
Chesterton Holidays
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Chesterton Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.


Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!
Reviewed on 16 Jul, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
It’s super convenient bc it’s on the pier but beware it’s connected so it’s not its own building. Still we felt safe and it was very clean
Reviewed on 16 Jul, 2025

Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.
Reviewed on 15 Jul, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
8.4/10 Very Good! (3,506 reviews)
Family of 6 got two rooms near one another on the same floor. A wonderful property in a great location. We loved it
Reviewed on 16 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 S$185 per night from 3 Aug to 4 Aug
S$185
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"The surroundings were beautiful and quiet. Liked how kitchy the building"
Reviewed on 11 Jul, 2025

Best Western Indian Oak
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is S$159 per night from 13 Aug to 14 Aug
S$159
13 Aug - 14 Aug
includes taxes & fees
8.4/10 Very Good! (1,013 reviews)
"Best Western Indian Oak – Chesterton, Indiana Where the Water’s Murky, and So is the Mood You’re not checking into the Best Western Indian Oak for the glamour. This isn't a destination. It's a pause—off the interstate, somewhere between where you were and where you’re going. A place with just enough ..."
Reviewed on 15 Jul, 2025

Hilton Garden Inn Chesterton
501 Gateway Boulevard, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is S$178 per night from 17 Aug to 18 Aug
S$178
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"We loved staying here."
Reviewed on 26 Jun, 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.
What to do in Chesterton

Indiana Dunes National Park Self-Guided Audio Tour
S$26
per traveller
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.