Chesterton Vacation Packages 2026 from $298

Chesterton flight + hotel vacation packages

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

Holiday Inn Express & Suites Prospect Heights by IHG

Save 100% on your flight

$298

per person

Sep 28 - Oct 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a 24-hour gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$627

per person

Oct 2 - Oct 6

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.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$778

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$522

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Omni Chicago Hotel

Downtown Chicago

Save 100% on your flight

$644

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's in-room fitness on site, and concierge services and wedding services are also offered.

Top Chesterton hotels deals

Waterbird Lakeside Inn

556 Indian Boundary Road Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$124 total

Jul 13 - Jul 14

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

Best Western Indian Oak

558 Indian Boundary Road Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$168 total

Jul 13 - Jul 14

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

Spring House Inn

303 N Mineral Springs Rd Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$161 total

Jul 13 - Jul 14

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

Furness Mansion

1491 N Furnleigh Ln Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$139 total

Jul 15 - Jul 16

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

Hilton Garden Inn Chesterton

501 Gateway Boulevard Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$178 total

Aug 3 - Aug 4

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 4 conference rooms, 24-hour business center, and express check-out. Enjoy the 24-hour gym and perks like free self parking.

Pool

Pet friendly

Quality Inn Chesterton near Indiana Dunes National Park I-94

418 Council Road Chesterton IN

Free Cancellation

$101 nightly

$113 total

Aug 10 - Aug 11

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

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

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.

See properties

Frequently asked questions

How much are vacation packages to Chesterton?

Treat yourself to an unforgettable experience in Chesterton with a vacation package starting at $298. 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.