Search Cheap Flights to
Hillside

Photo by Off The Beaten Track

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Hillside Flights as Low as $70

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Spirit Airlines
Frontier Airlines
Spirit Airlines
Frontier Airlines
United
Delta
American Airlines
Frontier Airlines
Delta
JetBlue Airways

Cheap Flights to Hillside

Fall in love at first flight with your vacation to Hillside by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Hillside on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Hillside, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Hillside

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Hillside with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Hillside?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Hillside are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Hillside?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Hillside.

What airport is best to fly into Hillside?

When you’re planning your trip to Hillside, convenience is the name of the game. Luckily, Hillside O'Hare Intl. Airport is nearby so you can deplane and get going on checking off everything on your Hillside must-do list.

How much are flights to Hillside?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Hillside on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $70, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Hillside?

The trick to saving a stack of cash on your flight to Hillside? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $70 right now, why wait?

Hillside Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$78

Last Minute Hotel Deals in Hillside

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $115 per night from Nov 24 to Nov 25
$115
includes taxes & fees
Nov 24 - Nov 25
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,067 reviews)
Spooky room!
"The room we were was hot and the AC couldn’t be turned on. A fan was brought to the room. There was a l it of running and screaming in the hallway for a couple of hours. The TV reception was staticky. Honestly, the room was a bit spooky."

Reviewed on Nov 1, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $144 per night from Nov 24 to Nov 25
$144
includes taxes & fees
Nov 24 - Nov 25
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,531 reviews)
"Location was ideal for walking to most river and city centre venues. The modernized room was very comfortable."

Reviewed on Nov 1, 2024

River Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
The price is $139 per night from Nov 24 to Nov 25
$139
includes taxes & fees
Nov 24 - Nov 25
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.2/10 Very Good! (3,159 reviews)
"Convenient location near great shops and dining options. Clean room, great complementary breakfast, and accessable and convenient valet parking."

Reviewed on Nov 1, 2024

Embassy Suites by Hilton Chicago Downtown River North
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
The price is $136 per night from Nov 24 to Nov 25
$136
includes taxes & fees
Nov 24 - Nov 25
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.4/10 Very Good! (3,254 reviews)
"The property is accessible and close to places I wanted to visit."

Reviewed on Oct 31, 2024

Club Quarters Hotel, Central Loop, Chicago
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is $182 per night from Nov 24 to Nov 25
$182
includes taxes & fees
Nov 24 - Nov 25
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,016 reviews)
expected more
"Noise level is high especially if you’re placed in an adjoining room. Bed comfortable, staff friendly and room service was fast and good quality food items. Cleanliness of bathroom was definitely subpar."

Reviewed on Nov 1, 2024

The Westin Michigan Avenue Chicago
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
The price is $112 per night from Nov 26 to Nov 27
$112
includes taxes & fees
Nov 26 - Nov 27
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (2,176 reviews)
"The location is great; the room is small"

Reviewed on Nov 1, 2024

citizenM Chicago Downtown
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
3.5 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
The price is $127 per night from Nov 26 to Nov 27
$127
includes taxes & fees
Nov 26 - Nov 27
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,165 reviews)
"Excellent, the best part is the people is so kind and friendly"

Reviewed on Oct 31, 2024

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
The price is $135 per night from Nov 26 to Nov 27
$135
includes taxes & fees
Nov 26 - Nov 27
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
7.8/10 Good! (1,214 reviews)
"The hotel was very nice but since it's downtown, there were a lot of sirens at noght. If you're a big city person it's probably no big deal but I don't like it"

Reviewed on Oct 31, 2024

Hotel Felix River North/Magnificent Mile
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.

Top Hotels With Free Airport Shuttle

Best Western Plus Chicago Hillside
Best Western Plus Chicago Hillside
3 out of 5
4400 Frontage Road, Hillside, IL
The price is $102 per night from Nov 10 to Nov 11
$102
includes taxes & fees
Nov 10 - Nov 11
Stay at this 3-star business-friendly hotel in Hillside. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
7.4/10 Good! (1,000 reviews)
"Nice"

Reviewed on Oct 30, 2024

Best Western Plus Chicago Hillside
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area
2.5 out of 5
200 S Mannheim Road, Hillside, IL
The price is $99 per night from Nov 10 to Nov 11
$99
includes taxes & fees
Nov 10 - Nov 11
Book a stay at this business-friendly hotel in Hillside. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
6.8/10 (1,002 reviews)
"Perfect location for our weekend in chicago"

Reviewed on Oct 20, 2024

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area
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.