Chesterton Vacations

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Find the Best Chesterton Vacation Packages

Chesterton Hotel Deals

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

2.5 out of 5
1800 West US Highway 20 Chesterton IN
Fully refundableReserve now, pay when you stay
The price is AED 347 per night from Jan 25 to Jan 26
AED 347
AED 389 total
25 Jan - 26 January 2026
includes taxes & fees
8/10 Very Good! (1,000 reviews)
Great staff and hospitality! Everything was clean and tidy.

Reviewed on 28 November 2025

Comfort Inn & Suites Porter near Indiana Dunes
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard Chesterton IN
Fully refundableReserve now, pay when you stay
The price is AED 452 per night from Jan 30 to Jan 31
AED 452
AED 506 total
30 Jan - 31 January 2026
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Very clean room Staff friendly

Reviewed on 7 December 2025

Hilton Garden Inn Chesterton
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
The price is AED 290 per night from Jan 12 to Jan 13
AED 290
AED 343 total
12 Jan - 13 January 2026
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
The Spring House Inn is a nice little spot near the dunes and we have stayed here many times. Much nicer than other hotels in the area. I only wish the beds had real comforters rather than those thin coverlets and more comfortable pillows.

Reviewed on 23 December 2025

Spring House Inn
See all 1,390 properties in Chesterton
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 which includes a sandy beach and general coastal views as well as a family

Indiana Dunes State Park

4.5/5(185 reviews)

You can take time to visit Indiana Dunes State Park during your travels to Chesterton. Wander the beautiful beaches and lakeside in the area.

Indiana Dunes State Park
This is a very nice place to hike.

Bailly Homestead - American Indians and Fur Traders

4.5/5(3 reviews)

You can find out about the history of Porter with a stop at Bailly Homestead - American Indians and Fur Traders. Wander the beautiful beaches and lakeside in the area.

Bailly Homestead - American Indians and Fur Traders
Michigan lake was a favorite stop and very much like the beach

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.

Waverly Beach

Frequently asked questions

How do I find cheap flights to Chesterton that have flexible change policies?
At Expedia, we've been channeling our inner yoga master to deliver you the most flexible airfares in town. Simply tick the "No change fee" box directly underneath the "Flexible change policies" filter to find your ideal flight to Chesterton.
Which airlines fly to Chesterton?
When it's time for a vacation, these popular airlines will make your journey to Chesterton super easy:

  • United Airlines - 13,009 flights to or near Chesterton each month, including 13,005 flights to O'Hare Intl. Airport (ORD) per month.
  • American Airlines - 10,036 flights to or near Chesterton each month, including 10,036 flights to O'Hare Intl. Airport (ORD) per month.

How can I find cheap tickets to Chesterton?
One of the best ways to get your hands on cheap tickets to Chesterton is to be flexible with your dates. Search for your flights, then click "flexible dates" above the results. It'll reveal the cheapest prices for nearby days. The lowest price for a flight to Chesterton in the last seven days was . Booking ahead of time will usually help you walk away with an even better deal.
How much is a flight to Chesterton?
One-way flights taking off from () sold for as low as in the last seven days. During this period, the price of a round-trip fare to Chesterton ranged between and . If you spot a bargain ticket, grab it fast — these prices don't stick around.
What are the most popular airports to fly into in Chesterton?
Depending on your budget, carrier and departure city, one of these busy airports will be your entry point to Chesterton:

  • O'Hare Intl. Airport (ORD) - 26,484 flights per month.
  • Midway Intl. Airport (MDW) - 6,439 flights per month.

When is the cheapest time to fly to Chesterton?
Fly out on a Tuesday to better your chances of picking up the cheapest fare to Chesterton. Mondays are usually the second most affordable day to take off. Saturday is normally the costliest day to fly anywhere.
How much is a plane ticket to Chesterton?
In the last seven days, plane fares to Chesterton fluctuated between and . Prices usually rise as your travel date nears, so grab a terrific deal today.
What months are the cheapest to book a flight to Chesterton?
To snap up an awesome deal to Chesterton, book sometime in February when airfares are at their cheapest. The most expensive time to book? In the United States, it's December.
How long is a flight to Chesterton?
Your flight to Chesterton could be short or long depending on where you leave from. Before you load up your tablet with TV shows and podcasts, have a look at the average flight times for these sought-after domestic routes:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 37 minutes
  • Denver, CO (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 34 minutes
  • Phoenix, AZ (PHX-Sky Harbor Intl.) to O'Hare Intl. Airport (ORD) - 3 hours and 17 minutes