Chesterton Holidays from £1,270
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
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.
Le Méridien Essex Chicago
Downtown Chicago
Price was £1,690, price is now £1,270 per person
£1,270
per person
29 Aug - 5 Sept
found 10 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Very clean and great view to the park. Staffs are helpful and respectful.
Reviewed on 20 Jun 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,854, price is now £2,098 per person
£2,098
per person
27 Aug - 3 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.
Reviewed on 24 Jun 2026
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was £3,210, price is now £2,382 per person
£2,382
per person
29 Aug - 5 Sept
found 10 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
We love the Peninsula! The staff, location, room, and the Shanghai restaurant top tier.
Reviewed on 21 Jun 2026
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was £3,341, price is now £2,483 per person
£2,483
per person
29 Aug - 5 Sept
found 10 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,011 reviews)
The spa was a terrific experience.
Reviewed on 22 Jun 2026
Kinzie Hotel
Downtown Chicago
Price was £1,675, price is now £1,278 per person
£1,278
per person
7 Sept - 14 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,146 reviews)
We enjoyed our stay at the Kinzie Hotel. A good location and helpful staff made for a nice visit!
Reviewed on 24 Jun 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
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
The price is £119 per night from 28 Jun to 29 Jun
£119
28 Jun - 29 Jun
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"Parking was right outside our room and we had a patio door which made getting items in and out very easy."
Reviewed on 23 Jun 2026
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
The price is £113 per night from 28 Jun to 29 Jun
£113
28 Jun - 29 Jun
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Older property that once was quite upscale. It has an interesting history. The room was clean, staff did their jobs, breakfast was minimal. The hotel shows its age and needs maintenance and upgrades."
Reviewed on 25 Jun 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
The price is £93 per night from 28 Jun to 29 Jun
£93
28 Jun - 29 Jun
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"The person checking us in was very pleasant and informative. However, the room definitively needed updating. There were places on the walls that had been primed but not painted and paint on the molding around the bathroom door. The view of the lake from the balcony was nice."
Reviewed on 23 Jun 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.
Explore a world of travel with Expedia
- Beverly Shores Hotels
- Hotels near Blue Chip Casino
- Burns Harbor Hotels
- Hobart Hotels
- Hotels near Indiana Dunes National Park
- Hotels near Indiana Dunes State Park
- Lake Station Hotels
- Long Beach Hotels
- Hotels with Indoor Pools in Michigan City
- Luxury Hotels in Michigan City
- Michigan City Hotels
- Holiday Homes in Michigan City
- Miller Beach Hotels
- Ogden Dunes Hotels
- Cheap Hotels in Portage
- Portage Hotels
- Porter Beach Hotels
- Caravan Parks in Porter
- Porter Hotels
- South Haven Hotels
- Hotels with Gym in Valparaiso
- Hotels with Restaurant in Valparaiso
- Valparaiso Hotels
- Hotels near Washington Park Zoo
- Westville Hotels
- Flights to Gary
- Flights to Michigan City
- Flights to Portage
- Flights to Valparaiso
- Flights from Valparaiso
- Flights from Westville
- Flights from Lake Station
- Flights from Portage
- Flights from Birmingham (BHX) to Michigan City (MGC)
- Flights from Boston (BOS) to Michigan City (MGC)
- Flights from Columbus (CMH) to Valparaiso (VPZ)
- Flights from Denver (DEN) to Michigan City (MGC)
- Flights from Dubai (DXB) to Michigan City (MGC)
- Flights from Indianapolis (IND) to Michigan City (MGC)
- Flights from New York (JFK) to Michigan City (MGC)
- Flights from New York (JFK) to Valparaiso (VPZ)
- Flights from Los Angeles (LAX) to Michigan City (MGC)
- Flights from London (LGW) to Michigan City (MGC)
- Flights from London (LHR) to Michigan City (MGC)
- Flights from Manchester (MAN) to Michigan City (MGC)
- Flights from Manchester (MAN) to Valparaiso (VPZ)
- Flights from Orlando (MCO) to Michigan City (MGC)
- Flights from Mexico City (MEX) to Michigan City (MGC)
- Flights from Miami (MIA) to Michigan City (MGC)
- Flights from Milwaukee (MKE) to Michigan City (MGC)
- Flights from Newcastle (NCL) to Michigan City (MGC)
- Flights from New York (NYC) to Michigan City (MGC)
- Flights from Chicago (ORD) to Michigan City (MGC)
- Flights from Santiago (SCL) to Valparaiso (VPZ)
- Flights from San Francisco (SFO) to Michigan City (MGC)
- Flights from Singapore (SIN) to Michigan City (MGC)
- Flights from Vancouver (YVR) to Michigan City (MGC)
- Flights from Toronto (YYZ) to Michigan City (MGC)
- Bremen Holidays
- Buffington Harbor
- Crown Point Sports Complex
- East Chicago Holidays
- Elkhart Holidays
- Gary Holidays
- Granger Holidays
- Grotto of Our Lady of Lourdes
- Hammond Civic Center
- Hammond Holidays
- Hanna Holidays
- Hebron Holidays
- Hobart Holidays
- Honeywell Center
- Knox Holidays
- Lafayette Holidays
- Ligonier Holidays
- Logansport Holidays
- Visit Long Beach
- Visit Tryon Farm
- Visit Michigan City
- Minden Bog
- Northwest Indiana Holidays
- Portage Lakefront Beach
- Portage Holidays
- Visit Portage
- South Bend Holidays
- St. Mary's College
- Swan Lake Resort
- Syracuse Holidays
- The Venue at Horseshoe Hammond
- Warsaw Holidays
- West Beach
- Winamac Holidays
* 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.
