Chesterton Holidays

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Chesterton Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
Good location and clean room

Reviewed on 17 Jul, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
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

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
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

Virgin Hotels Chicago

4.5 out of 5
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

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
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

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 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

Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
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

Best Western Indian Oak
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 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

Hilton Garden Inn Chesterton
See all 1,378 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.

What to do in Chesterton

Red Fox

Indiana Dunes National Park Self-Guided Audio Tour

S$26
per traveller
Indiana Dunes National Park Self-Guided Audio Tour
See all activities in Chesterton

Frequently asked questions

How much does a Chesterton holiday package cost?
You can grab a holiday package to this top destination from S$437 on Expedia. However, how much your holiday to Chesterton costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Chesterton?
If you're looking to book a cheap Chesterton holiday package, consider planning a trip in December, January and February. You'll typically find lower prices on hotels and flights during these months --- perfect for a budget-friendly getaway.
How many days is enough for Chesterton?
Typically, a few days is enough for a Chesterton holiday. With a carefully crafted itinerary, you can see all the top attractions like Coffee Creek Watershed Conservancy Preserve, as well as explore some hidden gems along the way.
Is it worth booking a holiday package to Chesterton?
From cool attractions such as Coffee Creek Watershed Conservancy Preserve and Lustron House to its terrific golfing, a Chesterton holiday guarantees an unforgettable adventure. With so much to see and do, find out for yourself why Chesterton is such a good holiday destination.
How to find the best Chesterton package deals?
Landing a cheap Chesterton package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Chesterton package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Chesterton holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking stays and flights individually. Better still, you can personalise your Chesterton trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Chesterton?
If you're considering an impromptu Chesterton holiday, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Chesterton?

  1. Choose when to go: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to escape to Chesterton.
  2. Set a budget: Consider expenses such as food, flights and transportation when working out how much to save for your trip to Chesterton. Then, pick a property that matches your budget, whether that's a low-cost stay or a lavish retreat.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to experience in Chesterton. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your airfare and accommodation: After you've nailed down your dates and duration, lock in the right Chesterton holiday package for you.

* 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.