Chesterton Holidays from AU$1,156
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Your Chesterton Holiday
Planning your next big travel adventure is easy with a Chesterton holiday package. The neighbourhood of Miller Beach, which is good for nature, makes a terrific base to uncover the treasures of this city. Want to start exploring your surroundings? Indiana Dunes National Park, Indiana Dunes State Park and Portage Lakefront Beach are just three of the top-rated places to visit during a trip to Chesterton. Whoever you're escaping with and whatever your bank balance, your dream Chesterton holiday is only clicks away with Expedia.
The Latest Chesterton Holiday Deals
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was AU$1,671, price is now AU$1,156 per person
AU$1,156
per person
12 Jan - 19 Jan
found 22 hours ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.
Reviewed on 8 Dec 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$3,270, price is now AU$2,044 per person
AU$2,044
per person
12 Jan - 19 Jan
found 22 hours ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Amazing hotel, location, staff, and food!!
Reviewed on 8 Dec 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was AU$1,908, price is now AU$1,239 per person
AU$1,239
per person
12 Jan - 19 Jan
found 22 hours ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city
Reviewed on 26 Nov 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was AU$1,745, price is now AU$1,185 per person
AU$1,185
per person
12 Jan - 19 Jan
found 22 hours ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Wife and I stayed here for 3 nights while visiting family. The Riu is a newer hotel and it shows! The place was modern, clean and well kept. Staff were really nice and helpful. They did an amazing job at the lobby bar and breakfast buffet. I was pleasantly surprised to see that the prices at the bar were on par or cheaper than local cocktail bars -$18 for an Wild Turkey 101 Old Fashioned! The breakfast buffet was a great bonus, we only waited a few minutes to be seated on Sat @10 am. Food was high quality and they provide a lot of options. All in all it was a really nice stay! Would definitely stay at a Riu hotel again and highly recommend to anyone else
Reviewed on 10 Dec 2025
Pendry Chicago
Downtown Chicago
Price was AU$1,909, price is now AU$1,319 per person
AU$1,319
per person
12 Jan - 19 Jan
found 22 hours ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man,
Neither would get me a cab, they said to just stand outside
Reviewed on 4 Dec 2025
Chesterton Holiday
Chesterton Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 13,400 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Indiana Dunes National Park, Indiana Dunes State Park and Lake View Beach |
Our pick of the best Chesterton Hotel Deals
Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20 Chesterton IN
Fully refundableReserve now, pay when you stay
The price is AU$153 per night from 21 Dec to 22 Dec
AU$153
21 Dec - 22 Dec
includes taxes & fees
8/10 Very Good! (1,000 reviews)
Great staff and hospitality! Everything was clean and tidy.
Reviewed on 28 Nov 2025
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
The price is AU$157 per night from 25 Dec to 26 Dec
AU$157
25 Dec - 26 Dec
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Beautiful Hotel
Reviewed on 5 Dec 2025
Hilton Garden Inn Chesterton
501 Gateway Boulevard Chesterton IN
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 25 Dec to 26 Dec
AU$173
25 Dec - 26 Dec
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Didn’t have and the room was plenty cool!
Reviewed on 9 Nov 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.
Discover the most popular places to visit in Chesterton
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.
Lustron House
Find out about the history of Chesterton with a stop at Lustron House. Wander the area's beautiful beaches or simply enjoy one of its cosy cafes.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
