Name: Best Western Indian Oak
Rating: 8.6

Your Chesterton Vacation

When you organize a vacation package to Chesterton, you can relax and enjoy your getaway knowing that all your travel arrangements have been made in advance. Discover the charms of this lively city from your base in a neighborhood like Miller Beach, which is great for nature. If your trip to Chesterton includes a little sightseeing, check out well-known attractions like Indiana Dunes State Park, Coffee Creek Watershed Conservancy Preserve and Portage Lakefront Beach. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Chesterton vacation is easy with Expedia.

The Latest Chesterton Vacation Packages

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

Hilton Chicago/Oak Brook Suites

Yorkfield

Save 100% on your flight

US$ 325

per person

Jun 1 - Jun 6

found 18 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7.8/10 Good! (1,004 reviews)

Front desk customer service was poor. At front desk with no line, clerk(s) did not greet us but one whom had the audacity to ask us to step aside and allow the women getting off the elevator to be helped first… Talked with them for 15mins about their check in, when we approached the desk first for the same thing. Clerk assisting him just shuffled around behind him, as if he didn’t want to help neither his coworker or us. Did not check us in until I got out of line from behind the first set of mentioned women & asked if he was able to check us in. Also everything I handed the second clerk he never returned in my hand only in front of me on the counter, very disrespectful in my opinion. First clerk: male, bald, with glasses. Second clerk: male, silver shoulder length hair & glasses.

Reviewed on 6 Mar, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

US$ 410

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (3,438 reviews)

the breakfast was ok like all the hotel. i like the international RIU better

Reviewed on 9 Mar, 2026

Thompson Chicago, by Hyatt

Downtown Chicago

Save 100% on your flight

US$ 1,172

per person

May 13 - May 20

found 1 hour ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,323 reviews)

Room was nice and clean, decent view. Perfect location. Close to shopping and nice restaurants. Staff was amazing; Myron in particular was so kind and accommodating.

Reviewed on 8 Mar, 2026

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

US$ 579

per person

May 22 - May 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (2,070 reviews)

Very nice & clean hotel and near the Bean and shops are walkable.

Reviewed on 3 Mar, 2026

Holiday Inn Chicago North-Evanston by IHG

Downtown Evanston

Save 100% on your flight

US$ 431

per person

Jun 1 - Jun 6

found 18 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,805 reviews)

Stayed just one night here with my mother, daughter, and her friend so my daughter and her friend could attend a concert nearby. Was super happy with the cleanliness of the hotel, the comfort of the beds, and the kind staff. Only minor complaint would be that the doors slam throughout which could be a little frustrating if you are a light sleeper and the parking garage is a little tight and could be really bad for someone with a low to ground car due to the super steep entrance/exit ramp. Lastly, I was under the impression that there was a bar/restaurant on site. Unfortunately, there is only the dining area for the paid breakfast or dinner. Aside from those few minor things, I would highly recommend this place. I will be returning in the summer as it's nice and close to the shore and beaches too.

Reviewed on 6 Mar, 2026

Things to do in and around Chesterton

Chesterton, Indiana, offers a perfect blend of outdoor adventure and scenic beauty. Visitors can explore popular attractions like local parks, enjoy nature walks, and take advantage of biking trails. The recreational areas and playgrounds make it an ideal destination for families, while nature enthusiasts will appreciate the opportunity for little sightseeing and exploration of the area's natural landscapes.

Shopping

In Chesterton, you can shop at local boutiques and specialty stores. If you're up for a drive, visit Lighthouse Place Premium Outlets for a variety of shops, or explore Westfield Southlake Mall for more options and entertainment. Garwood Orchards offers unique gifts and local produce.

Recreation

Explore Marquette Park for a serene day surrounded by nature, perfect for relaxation and mindfulness. Experience the charm of Chicago Street Theatre for an evening filled with culture and entertainment. For outdoor enthusiasts, enjoy a round of disc golf at the nearby Disc Golf Course, embracing friendly competition.

Adventure

Experience thrills at Deep River Water Park, located 13 miles from Chesterton, where you can enjoy exciting water slides and family fun. For an adrenaline rush, visit Team Combat LIVE, 14 miles away, featuring immersive arcade battles. Don’t miss the scenic Cowles Bog Trailhead, perfect for hiking right in Chesterton.

Nightlife

Experience a unique nightlife in Chesterton with a visit to the Round Barn Union Pier Tasting Room, located 25 miles away. Enjoy a cozy pub atmosphere filled with entertainment and romantic vibes, perfect for unwinding after a day of exploration.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Chesterton

Chesterton, Indiana, is a fantastic destination for outdoor enthusiasts and families alike, offering beautiful scenery and adventure opportunities. Visitors can explore the stunning beaches and trails of the nearby Indiana Dunes National Park, as well as enjoy the local urban parks. With various attractions catering to outdoor activities and family experiences, Chesterton promises a memorable getaway for all types of travelers.

Indiana Dunes National Park: Just 3 miles from Chesterton, this national park offers breathtaking scenery and a variety of outdoor adventures. Explore miles of sandy beaches, hike scenic trails, and enjoy the diverse ecosystems that make this park a natural wonder.
Lake View Beach: Located 6 miles away, Lake View Beach is a serene spot perfect for relaxing under the sun. With its soft sands and stunning views of Lake Michigan, it’s an ideal place for swimming, picnicking, or simply soaking in the beach vibes.
Indiana Dunes Visitor Center: Situated within Chesterton, this visitor center is your gateway to adventure. Families can learn about the park's natural history and find resources for exploring the surrounding outdoor wonders, making it a great starting point for your trip.

Tips to save on your trip to Chesterton

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling during the off-peak season (typically January to February and November) for more affordable package holidays to Chesterton.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Language

English

Currency

U.S dollars

Population

13,400

Max Temp Winter

30ºF

Max Temp Summer

75ºF

Top Sights

Indiana Dunes National Park, Indiana Dunes State Park and Lake View Beach

Chesterton Hotel Deals

Comfort Inn & Suites Porter near Indiana Dunes

1800 West US Highway 20 Chesterton IN

Fully refundableReserve now, pay when you stay

8/10 Very Good! (1,007 reviews)

Staff gave us a nice quiet room .. thanks so much! Breakfast left a lot to be desired. No yogurt variety.. no oatmeal variety.. rolls were dry.. no fruit variety.. no meat or egg variety.. pretty blah.. kids had taken over pool we couldn’t get in..

Reviewed on 9 Mar, 2026

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Spring House Inn

303 N Mineral Springs Rd Chesterton IN

Fully refundableReserve now, pay when you stay

8.8/10 Excellent! (1,004 reviews)

I have been wanting to try this place for a while now and decided to finally go and I'm glad we did. Check in was smooth and quick. Staff was friendly and helpful. Pool was warm and relaxing. Sauna felt great. The room we stayed in had a jetted tub and balcony. Bed was very comfortable and pillows ...

Reviewed on 9 Mar, 2026

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Best Western Indian Oak

558 Indian Boundary Road Chesterton IN

Fully refundableReserve now, pay when you stay

8.6/10 Excellent! (1,007 reviews)

This is my family's favorite place to stay when we visit This part of indiana. Always on point. Breakfast on point. Cleanliness on point. Pool on point. Sauna on Point. Staff on point........EVERYTHING on POINT.

Reviewed on 9 Mar, 2026

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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.