Name: Waterbird Lakeside Inn
Price range: CA $155
Rating: 8.2

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.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $913

per person

Sep 10 - Sep 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.2/10 Very Good! (2,767 reviews)

No drinking glasses in my room. No pen/pencil and paper

Reviewed on Jun 22, 2026

Level Chicago - River North

Downtown Chicago

CA $1,251

per person

Jul 28 - Jul 31

found 4 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,034 reviews)

Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,687

per person

Sep 14 - Sep 17

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (2,557 reviews)

The people at the front desk were extremely helpful. Everyone was super kind & you never really have to leave the hotel.. plenty of shops and restaurants right there in the hotel! Breakfast was not included, but there is breakfast on site.. there’s cheap breakfast and expensive breakfast all depends on what you are in the mood for. Wonderful stay over all!!!

Reviewed on Jun 22, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,412

per person

Jul 24 - Jul 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (498 reviews)

This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.

Reviewed on Jun 20, 2026

Level Chicago – Old Town

Downtown Chicago

CA $1,217

per person

Sep 14 - Sep 17

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9/10 Wonderful! (489 reviews)

We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Ready to book your vacation to Chesterton?

Choose your dates

Chesterton Hotel Deals

Best Western Indian Oak

558 Indian Boundary Road Chesterton IN

Fully refundableReserve now, pay when you stay

CA $198

CA $222 total

Jun 23 - Jun 24

includes taxes & fees

8.6/10 Excellent! (1,007 reviews)

"This was such a peaceful visit and we loved the lakeside room. The pool was a bit dirtier than I would like but I blame that more on other guests than the hotel."

Reviewed on Jun 21, 2026

Spring House Inn

303 N Mineral Springs Rd Chesterton IN

Fully refundableReserve now, pay when you stay

CA $183

CA $212 total

Jun 23 - Jun 24

includes taxes & fees

9/10 Wonderful! (1,005 reviews)

"Just a wonderful stay especially for the price. Hotel is set off the main highway in the woods. We had a king bed room, it was huge and very comfortable with a balcony overlooking the woods. Dining room was very nice and a very good breakfast. Oh yes, indoor heated pool and sauna! Sad we stayed only ..."

Reviewed on Jun 22, 2026

Waterbird Lakeside Inn

556 Indian Boundary Road Chesterton IN

Fully refundableReserve now, pay when you stay

CA $155

CA $173 total

Jun 23 - Jun 24

includes taxes & fees

8.2/10 Very Good! (1,002 reviews)

"This location is old but clean. It was also very quiet as there seemed to be few customers. We stayed 3 nights while enjoying the convenient location to the Indiana Dunes National Park and a lot of nice restaurant options. The beds were comfortable. It was nice having a balcony overlooking a small ..."

Reviewed on Jun 19, 2026

See all 1,437 properties in Chesterton

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.