Chesterton Vacations from ₩658,370

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Chesterton Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩1,093,109, price is now ₩658,370 per person
₩658,370
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.

Reviewed on Feb 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩1,871,151, price is now ₩981,112 per person
₩981,112
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all

Reviewed on Feb 2, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩1,386,306, price is now ₩853,440 per person
₩853,440
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Every detail. The staff was amazing.

Reviewed on Jan 30, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩1,547,730, price is now ₩963,462 per person
₩963,462
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩1,377,780, price is now ₩868,557 per person
₩868,557
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
9.6/10 Exceptional! (1,067 reviews)
always clean, great staff comfortable beds good location

Reviewed on Feb 1, 2026

Find the Best Chesterton Vacation Packages

Chesterton Hotel Deals

Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

2.5 out of 5
1800 West US Highway 20 Chesterton IN
Fully refundableReserve now, pay when you stay
The price is ₩109,700 per night from Feb 24 to Feb 25
₩109,700
₩122,864 total
Feb 24 - Feb 25
includes taxes & fees
8/10 Very Good! (999 reviews)
Great staff and hospitality! Everything was clean and tidy.

Reviewed on Nov 28, 2025

Comfort Inn & Suites Porter near Indiana Dunes
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
The price is ₩114,558 per night from Feb 5 to Feb 6
₩114,558
₩135,556 total
Feb 5 - Feb 6
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)
Nice quiet hotel, very clean, good looking pool (we didn’t swim), breakfast was ok. Outstanding value!

Reviewed on Jan 27, 2026

Spring House Inn
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
8/10 Very Good! (996 reviews)
Clean room. Jet tub was clean and relaxing.

Reviewed on Jan 26, 2026

Get rates
Waterbird Lakeside Inn
See all 1,413 properties in Chesterton
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.

Discover the most popular places to visit in Chesterton

Indiana Dunes National Park Sign

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.

Indiana Dunes Visitor Center

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.