Chesterton Holidays from £1,248
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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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £1,801, price is now £1,248 per person
£1,248
per person
17 Jun - 22 Jun
found 16 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,655 reviews)
If you’re up for walking, this hotel is a great place to stay close enough to most things.
Reviewed on 8 May 2026
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was £3,164, price is now £1,993 per person
£1,993
per person
31 Jul - 6 Aug
found 12 hours ago
Return direct flight included
Leeds (LBA) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
The view is fantastic. You can see the Chicago river on one side, abd skyscraper on tge other side. The small items that the hotel provides, makes the stay, pleasant and homely.
Reviewed on 10 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £2,154, price is now £1,456 per person
£1,456
per person
17 Jun - 22 Jun
found 16 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on 8 May 2026
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was £3,412, price is now £2,347 per person
£2,347
per person
31 Jul - 6 Aug
found 12 hours ago
Return direct flight included
Leeds (LBA) to Chicago (ORD)
9.2/10 Wonderful! (973 reviews)
Room was pretty dirty. Told front desk and said they were sending housekeeping but never did. Front desk clerk wasn’t very kind.
Reviewed on 10 May 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
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
The price is £101 per night from 12 May to 13 May
£101
12 May - 13 May
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Notice it wasn’t as nice as previous stays. No hot chocolate, not much for breakfast, etc. BUT woke up to mice and mice poop took it over the edge.
Reviewed on 5 May 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
The price is £77 per night from 19 May to 20 May
£77
19 May - 20 May
includes taxes & fees
8.6/10 Excellent! (1,011 reviews)
Parking was safe , Breakfast was good
Reviewed on 10 May 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
The price is £75 per night from 12 May to 13 May
£75
12 May - 13 May
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
Yes
Reviewed on 7 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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* 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.
