- Better togetherSave up to ฿3,170 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
Plan, book, travel with confidence
Top Chesterton Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
per person
3 Jul - 7 Jul
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
7.8/10 Good! (1,013 reviews)
The bathroom could have been cleaner, the air conditioning barely worked which made the room incredibly hot. The lobby is nice enough, and the staff is super friendly. The location is wonderful.
Reviewed on 11 May 2024
Pendry Chicago
Downtown Chicago
per person
3 Jul - 7 Jul
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (679 reviews)
Enjoyed our stay at the Pendry. It is in a great location and very walkable. Housekeeping was great. Enjoyed the restaurant and bar and the staff was very friendly.
Reviewed on 15 May 2024
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
3 Jul - 7 Jul
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
8.8/10 Excellent! (206 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.
Reviewed on 16 Mar 2024
Top hotels in Chesterton
Waterbird Lakeside Inn
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is ฿3,292 per night from 19 May to 20 May
฿3,292
per night
19 May - 20 May
7.8/10 Good! (698 reviews)
"We’ve stayed here many times. The only concern is the sometimes spotty wi-fi. Always comfortable and the wildlife is entertaining, especially the turtles and swallows. Will return."
Reviewed on 13 May 2024
Best Western Indian Oak
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is ฿4,023 per night from 19 May to 20 May
฿4,023
per night
19 May - 20 May
8.4/10 Very Good! (978 reviews)
"Over very good"
Reviewed on 14 May 2024
Spring House Inn
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is ฿3,987 per night from 16 May to 17 May
฿3,987
per night
16 May - 17 May
8.8/10 Excellent! (882 reviews)
"Setting in trees; beautiful unique hotel building. Good breakfast."
Reviewed on 13 May 2024
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
Popular places to visit
Indiana Dunes State Park
4/5(1 review)
The southern shores of Lake Michigan consist of a stunning dune landscape, which is ideal for hiking, camping, bird-watching, picnicking and swimming.
Bailly Homestead - American Indians and Fur Traders
You can find out about the history of Porter with a trip to Bailly Homestead - American Indians and Fur Traders. Wander the beautiful beaches and lakeside in the area.
Waverly Beach
Why not spend a lazy afternoon at Waverly Beach during your trip to Chesterton? Stroll along the beaches or visit the shops in the area.
More trip options
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.