Chesterton Holidays from £761
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Your Chesterton Holiday
When you organise a holiday 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 neighbourhood 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, organising your ultimate tailored Chesterton holiday is easy with Expedia.
Top Chesterton Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The Wade
Downtown Chicago
Price was £1,090, price is now £761 per person
£761
per person
24 Apr - 1 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
I had a great stay at the Wade Hotel in Chicago! The room was very clean and comfortable, and the staff was friendly, professional, and welcoming from check-in to check-out. The amenities were convenient, and the location made it easy to get around the city. I would definitely stay here again and recommend it to anyone visiting Chicago.
Reviewed on 9 Feb 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was £1,398, price is now £937 per person
£937
per person
24 Apr - 1 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Service was amazing and the location was perfect. Would definitely stay here again.
Reviewed on 28 Jan 2026
Arlo Chicago
Downtown Chicago
Price was £1,168, price is now £814 per person
£814
per person
24 Apr - 1 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Room was clean but the soap dispenser at the sync and in shower were not working as it supposed to.
Reviewed on 5 Feb 2026
Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,482, price is now £1,041 per person
£1,041
per person
30 Apr - 6 May
found 8 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Staff was super friendly and rooms were clean. Definitely will come back
Reviewed on 20 Jan 2026
Chesterton Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 13,400 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Indiana Dunes National Park, Indiana Dunes State Park and Lake View Beach |
Top hotels in Chesterton
Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20 Chesterton IN
Fully refundableReserve now, pay when you stay
The price is £62 per night from 1 Mar to 2 Mar
£62
1 Mar - 2 Mar
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Clean room
Reviewed on 6 Feb 2026
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
The price is £69 per night from 10 Feb to 11 Feb
£69
10 Feb - 11 Feb
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
Cute wallpaper, quaint
Reviewed on 2 Feb 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
8/10 Very Good! (997 reviews)
Clean room. Jet tub was clean and relaxing.
Reviewed on 26 Jan 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. Flight-inclusive packages are ATOL protected.
