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.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,039, price is now CA $707 per person
CA $707
per person
May 1 - May 3
found 3 hours 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
La Banque Hotel
Price was CA $1,044, price is now CA $743 per person
CA $743
per person
Apr 9 - Apr 12
found 1 day 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
Downtown Chicago
Price was CA $1,064, price is now CA $778 per person
CA $778
per person
Mar 31 - Apr 4
found 13 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
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,209, price is now CA $885 per person
CA $885
per person
Mar 15 - Mar 19
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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,950, price is now CA $1,433 per person
CA $1,433
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Chesterton Hotel Deals
Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20 Chesterton IN
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Mar 1 to Mar 2
CA $104
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
Spring House Inn
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
Waterbird Lakeside Inn
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
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
