Chesterton Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
Photo by Indiana Office of Tourism Development
- Plan, book, travel with confidence
- Better togetherSave up to ฿4,531 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Chesterton Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ฿57,241, price is now ฿32,185 per person
฿32,185
per person
13 Dec - 18 Dec
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
FOOD WAS GOOD, JUST A LITTLE COLD, BUT NO MAJOR PROBLEMS
Reviewed on 12 Nov 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was ฿29,565, price is now ฿16,699 per person
฿16,699
per person
13 Dec - 18 Dec
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.
Reviewed on 12 Nov 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ฿24,759, price is now ฿14,508 per person
฿14,508
per person
13 Dec - 18 Dec
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
The breakfast exceeded my expectations. I loved this hotel. Everything was great I will be staying again.
Reviewed on 13 Nov 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was ฿29,352, price is now ฿17,405 per person
฿17,405
per person
13 Dec - 18 Dec
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on 9 Nov 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 ฿3,203 per night from 17 Nov to 18 Nov
฿3,203
฿3,749 total
17 Nov - 18 Nov
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
All around excellent
Reviewed on 10 Nov 2025
Best Western Indian Oak
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is ฿3,025 per night from 19 Nov to 20 Nov
฿3,025
฿3,388 total
19 Nov - 20 Nov
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
Our room was clean and spacious! Loved the lake view! Liked the lotion and shampoo! Breakfast was average...wish they'd serve real eggs and make hot oatmeal in the pot. Enjoyed the yogurt machine! Muffins were artificial tasting. Coffee was great!
Reviewed on 10 Nov 2025
Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is ฿2,974 per night from 14 Dec to 15 Dec
฿2,974
฿3,331 total
14 Dec - 15 Dec
includes taxes & fees
8/10 Very Good! (1,001 reviews)
My room was clean and comfortable. I would definitely stay here again
Reviewed on 28 Oct 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.
Popular places to visit
Indiana Dunes State Park
The southern shores of Lake Michigan consist of a stunning dune landscape, which is ideal for hiking, camping, bird-watching, picnicking and swimming.
More trip options
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
