Chesterton Holidays
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Top Flight + Hotel Deals in Chesterton
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was €1,602, price is now €1,341 per person
€1,341
per person
10 Jul - 13 Jul
found 2 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
8.8/10 Excellent! (2,148 reviews)
Lovely stay and we are at Toro right in the hotel. Fabulous dinner
Reviewed on 18 May 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €2,084, price is now €1,682 per person
€1,682
per person
10 Jul - 13 Jul
found 2 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Great experience! Would stay here agin
Reviewed on 18 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €1,886, price is now €1,522 per person
€1,522
per person
10 Jul - 13 Jul
found 2 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
I loved it here and will definitely stay again.
Reviewed on 18 May 2026
Swissotel - Chicago
Downtown Chicago
Price was €1,651, price is now €1,349 per person
€1,349
per person
10 Jul - 13 Jul
found 2 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9/10 Wonderful! (3,319 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.
Reviewed on 16 May 2026
Pendry Chicago
Downtown Chicago
Price was €1,862, price is now €1,549 per person
€1,549
per person
10 Jul - 13 Jul
found 2 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.2/10 Wonderful! (1,126 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on 27 Apr 2026
Top hotels in Chesterton
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
The price is €119 per night from 20 May to 21 May
€119
20 May - 21 May
includes taxes & fees
8.8/10 Excellent! (1,016 reviews)
"Staff great......confusing to get around.. But worth it!!!"
Reviewed on 18 May 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
The price is €98 per night from 31 May to 1 Jun
€98
31 May - 1 Jun
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Don’t sleep on this hidden gem. Most comfortable sleep we’d had in ages, so much so that we asked what brand the mattress was. Easy on and off, with lots of amenities nearby. If in the area, we would absolutely stay here again."
Reviewed on 18 May 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
The price is €88 per night from 20 May to 21 May
€88
20 May - 21 May
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Great price, nice quiet room with awesome view"
Reviewed on 14 May 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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