Chesterton Vacation Packages 2026 from $618

Chesterton flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$618

per person

Oct 13 - Oct 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$646

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$1,010

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$796

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$756

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

Top Chesterton hotels deals

Spring House Inn

303 N Mineral Springs Rd Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$109 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like self-serve breakfast and free self parking.

Pool

Breakfast included

Best Western Indian Oak

558 Indian Boundary Road Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$124 total

Sep 20 - Sep 21

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Enjoy the sauna and perks like free self parking and free WiFi. A 24-hour business center, a lobby fireplace, and express check-out are also on offer.

Pool

Breakfast included

Waterbird Lakeside Inn

556 Indian Boundary Road Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$128 total

Sep 14 - Sep 15

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, express check-out, and laundry facilities are also on offer.

Parking included

Free WiFi

Quality Inn Chesterton near Indiana Dunes National Park I-94

418 Council Road Chesterton IN

Free Cancellation

$94 nightly

$105 total

Sep 27 - Sep 28

Total with taxes and fees

A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

Breakfast included

Parking included

Comfort Inn & Suites Porter near Indiana Dunes

1800 West US Highway 20 Chesterton IN

Free Cancellation

$113 nightly

$127 total

Oct 8 - Oct 9

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.

Pool

Hot Tub

Furness Mansion

1491 N Furnleigh Ln Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$135 total

Oct 13 - Oct 14

Total with taxes and fees

This hotel features a garden, laundry facilities, and free self parking. A picnic area and barbecue grills are also provided.

Spa

Pet friendly

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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 wooden staircase leading up a sandy hill with dense green forest in the background.

Indiana Dunes State Park

9.0/10 (717 reviews)

The southern shores of Lake Michigan consist of a stunning dune landscape, which is ideal for hiking, camping, bird-watching, picnicking and swimming.

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Frequently asked questions

How much are vacation packages to Chesterton?

Treat yourself to an unforgettable experience in Chesterton with a vacation package starting at $618. Locking in your flights, tours and hotels with Travelocity is so easy. What's more, our vacation deals will leave you with extra money for loads of fun activities.

How long should my Chesterton vacation be?

Your Chesterton getaway can be as short or as long as you'd like it to be, but the majority of people stay roughly 2 nights. Want to get out and uncover some lesser-known sights? Stay a few extra nights and see a different side of this destination.

Where can I get the best vacation package deals for Chesterton?

There are awesome Chesterton package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties around the globe? Keep this in mind when you're ready to check another destination off your list.

Why should I book my Chesterton vacation package with Travelocity?

Whether you're planning a weeks-long vacation or a last-minute trip, we have plenty of amazing destinations to choose from at a good price. What's more, we offer 24/7 support, excellent service and a Price Match Guarantee. Save yourself time and money and reserve your dream vacation today.

Will I save money on my Chesterton car rental if I book it with my hotel or flight?

Bundling your hotel, flight and car into a Chesterton vacation package is an excellent way to score an amazing deal. Plus, having your own set of wheels gives you freedom to make your way to all those amazing sights you're itching to see. Located 40 mi from Chesterton, Wrigley Field is one place that should be on your must-do list. Turn up the tunes and make a day trip of it.

Which airport is best for Chesterton?

O'Hare Intl. Airport (ORD) is popular. You'll find it approximately 50 mi northwest of Chesterton. Your other options are Midway Intl. Airport (MDW) (35 mi away from central Chesterton) and South Bend Intl. Airport (SBN) (40 mi away from central Chesterton).

What is there to do in Chesterton?

You'll notice a certain magic as you stroll the streets of Chesterton. Dune Acres Beach and Coffee Creek Watershed Conservancy Preserve are just a couple of highlights that entice visitors to this wonderful city, so put them on your list of places to see.

Where should I stay when visiting Chesterton?

Many visitors opt to hit the hay at the Spring House Inn. It's a terrific base for your Chesterton vacation.