Chesterton Holidays

Photo by City Circus Wandering

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Top Flight + Hotel Deals in Chesterton

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Loved the old time and modern vibe.

Reviewed on 9 Aug 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
This was my first time staying. The staff was very friendly and helpful. Our room was very nice and perfectly located downtown. Also, the breakfast buffet was amazing and a nice surprise.

Reviewed on 9 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Really nice and amazing location!! Would stay again!

Reviewed on 9 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (332 reviews)
A lot of good food options walkable distance.

Reviewed on 3 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
I liked this hotel, the rooms are cleaning and beautiful, the staff is nice, and the hotel is located near amazing restaurants, cafes, and tourist places.

Reviewed on 9 Aug 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 €109 per night from 2 Sept to 3 Sept
€109
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Friendly staff. Clean room. Drapes made the room dark and nice for sleeping in! Nice breakfast choices. Pool was closed for maintenance for part of one day, but fixed in a very timely manner to open by that evening. Staff addressed any concerns we had (one key card didn’t work and one wouldn’t open ..."

Reviewed on 8 Aug 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 €98 per night from 1 Sept to 2 Sept
€98
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"Loved the lake"

Reviewed on 7 Aug 2025

Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
8/10 Very Good! (899 reviews)
"Nice and clean place to stay!"

Reviewed on 7 Aug 2025

Get rates
Waterbird Lakeside Inn
See all 1,368 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.

Frequently asked questions

How much does a Chesterton holiday package cost?
You can grab a holiday package to this top destination from €805 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.