Chesterton Vacation Packages 2026 from $489

Chesterton flight + hotel vacation packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$489

per person

Jun 17 - Jun 20

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$676

per person

Jun 17 - Jun 20

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$618

per person

Jun 19 - Jun 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Save 100% on your flight

$514

per person

Jun 17 - Jun 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 15 conference rooms on site, along with the valet parking and WiFi in public areas. Self parking, a lobby fireplace, and luggage storage are also offered.

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Save 100% on your flight

$862

per person

Jun 19 - Jun 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, 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 terrace, a snack bar/deli, and a free grocery shopping service are also on offer.

Top Chesterton hotels deals

Spring House Inn

303 N Mineral Springs Rd Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$105 total

Apr 6 - Apr 7

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

$89 nightly

$100 total

Apr 12 - Apr 13

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.

Comfort Inn & Suites Porter near Indiana Dunes

1800 West US Highway 20 Chesterton IN

Free Cancellation

$88 nightly

$98 total

Apr 26 - Apr 27

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

Hilton Garden Inn Chesterton

501 Gateway Boulevard Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$136 total

Apr 12 - Apr 13

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.

Waterbird Lakeside Inn

556 Indian Boundary Road Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$91 total

Apr 6 - Apr 7

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

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Porter IN

Get rates

This cabin featured laundry facilities and barbecue grills.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Chesterton

View all properties

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.

Popular places to visit

Indiana Dunes State Park

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

Indiana Dunes Visitor Center

Explore the great outdoors at Indiana Dunes Visitor Center, a lovely green space in Porter. Wander the beaches and forest in this family-friendly area.

Waverly Beach

Why not spend a lazy afternoon at Waverly Beach during your trip to Chesterton? Stroll along the beaches or visit the shops in the area.

Frequently asked questions

How much are vacation packages to Chesterton?

Treat yourself to an unforgettable experience in Chesterton with a vacation package starting at $489. 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.