Chesterton Vacation Packages 2026 from $418

Chesterton flight + hotel vacation packages

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

Thompson Chicago, by Hyatt

Downtown Chicago

$418

per person

May 3 - May 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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

JW Marriott Chicago

Downtown Chicago

Save 100% on your flight

$469

per person

Apr 30 - May 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Level Chicago – Old Town

Downtown Chicago

$520

per person

May 3 - May 6

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.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$479

per person

Apr 30 - May 3

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, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

$456

per person

May 7 - May 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

Top Chesterton hotels deals

Comfort Inn & Suites Porter near Indiana Dunes

1800 West US Highway 20 Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$90 total

Feb 23 - Feb 24

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

Spring House Inn

303 N Mineral Springs Rd Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$83 nightly

$93 total

Feb 19 - Feb 20

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

Waterbird Lakeside Inn

556 Indian Boundary Road Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$86 total

Feb 19 - Feb 20

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

Hilton Garden Inn Chesterton

501 Gateway Boulevard Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$112 total

Mar 1 - Mar 2

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

Best Western Indian Oak

558 Indian Boundary Road Chesterton IN

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$94 total

Feb 19 - Feb 20

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

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

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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.

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.

Coffee Creek Watershed Conservancy sign in Chesterton, Indiana USA

Coffee Creek Watershed Conservancy Preserve

Explore the great outdoors at Coffee Creek Watershed Conservancy Preserve, a lovely green space in Chesterton. Wander the area's beautiful beaches or simply enjoy one of its charming coffeehouses.

Frequently asked questions

How much are vacation packages to Chesterton?

Treat yourself to an unforgettable experience in Chesterton with a vacation package starting at $418. 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.