Chesterton Vacation Packages

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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.

Top Chesterton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $975, price is now CA $661 per person
CA $661
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (766 reviews)
Great stay. Would come again.

Reviewed on Jan 19, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,039, price is now CA $707 per person
CA $707
per person
May 1 - May 3
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.

Reviewed on Jan 6, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $959, price is now CA $679 per person
CA $679
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was friendly, and room was cleaned well. Free breakfast was also a nice touch and better than expected

Reviewed on Feb 6, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,044, price is now CA $743 per person
CA $743
per person
Apr 9 - Apr 12
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was CA $1,064, price is now CA $778 per person
CA $778
per person
Mar 31 - Apr 4
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Room and customer service was great!

Reviewed on Jan 20, 2026

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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 CA $103 per night from Mar 1 to Mar 2
CA $103
CA $116 total
Mar 1 - Mar 2
includes taxes & fees
8/10 Very Good! (1,000 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 CA $108 per night from Feb 8 to Feb 9
CA $108
CA $128 total
Feb 8 - Feb 9
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Cute wallpaper, quaint

Reviewed on Feb 2, 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

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Waterbird Lakeside Inn
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