Chesterton Vacations from ￥280,564

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The Latest Chesterton Vacation 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
Price was ￥338,731, price is now ￥280,564 per person
￥280,564
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
I thoroughly enjoyed my stay at Hotel Felix! While it may not technically be a five-star luxury chain, it definitely gave us five-star hotel vibes thanks to the incredible staff and the fantastic extra perks.The location is absolutely awesome. It puts you about a mile or so from all the major hotspots, including Navy Pier, the Riverwalk, and the Magnificent Mile. There are tons of excellent places to eat right nearby, and having a Divvy bike rental station right down the street made exploring the city incredibly easy.The service from the staff was top-notch from start to finish. I highly recommend this hotel for anyone looking for a stylish, perfectly located, and highly accommodating place to stay in Chicago!

Reviewed on Jul 13, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥417,913, price is now ￥311,530 per person
￥311,530
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Great location, clean, rooftop bar and great staff.

Reviewed on Jul 13, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was ￥382,081, price is now ￥300,700 per person
￥300,700
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Main area was nice. Hotel room was outdated

Reviewed on Jul 13, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥379,612, price is now ￥309,040 per person
￥309,040
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
Probably the best hotel I ever stayed at next time. Make sure I get a room with a view of the lake for five stars.

Reviewed on Jul 12, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥379,093, price is now ￥316,714 per person
￥316,714
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)
The staff was so nice and they even upgraded me to a suite for my daughter's sweet 16. A suite for a sweet. Very appreciative. I have stayed at a few hotels downtown, but I keep going back for the views! Thank you Swissotel.

Reviewed on Jul 13, 2026

Find the Best Chesterton Vacation Packages

Chesterton Hotel Deals

Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
The price is ￥17,654 per night from Jul 15 to Jul 16
￥17,654
￥19,772 total
Jul 15 - Jul 16
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Room was big and had a nice lake view. Some of the outlets and lights were not working in the room."

Reviewed on Jul 8, 2026

Waterbird Lakeside 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 ￥24,250 per night from Jul 14 to Jul 15
￥24,250
￥27,161 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (1,016 reviews)
"Place was clean and convenient. We would stay again."

Reviewed on Jul 12, 2026

Best Western Indian Oak
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 ￥22,474 per night from Jul 15 to Jul 16
￥22,474
￥25,979 total
Jul 15 - Jul 16
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"It was quiet and the bed was comfortable. It is an old inn and cute, but needs updated and fixed up."

Reviewed on Jul 13, 2026

Spring House Inn
See all 1,452 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.

Stay near popular Chesterton attractions

A sandy beach with the ocean in the background and a grassy hill with trees.

Indiana Dunes State Park

9.0/10 (717 reviews)
Towering sand dunes rise nearly 200 feet above Lake Michigan's pristine shoreline. Hike the 16.5 miles of trails through diverse ecosystems or relax on the beach with panoramic lake views.
See properties

Frequently asked questions

How much does a Chesterton vacation package cost?
You can grab a vacation package to this top destination from ￥280,564 on Expedia. However, how much your vacation 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 vacation 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 vacation. 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 vacation package to Chesterton?
From cool attractions such as Coffee Creek Watershed Conservancy Preserve and Lustron House to its terrific golfing, a Chesterton vacation guarantees an unforgettable adventure. With so much to see and do, find out for yourself why Chesterton is such a good vacation 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," "Traveler 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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Chesterton vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking stays and flights individually. Better still, you can personalize 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 vacation package to Chesterton?
If you're considering an impromptu Chesterton vacation, 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 accommodations: After you've nailed down your dates and duration, lock in the right Chesterton vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.