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Hillside

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Hillside Flights as Low as $112

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

Frontier Airlines
Tue, Jul 29 - Thu, Aug 7
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 4 days ago
$112
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Jul 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 7, priced at $112 found 4 days ago
Spirit Airlines
Wed, Jul 30 - Wed, Aug 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 4 hours ago
$112
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Wed, Jul 30 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $112 found 4 hours ago
Spirit Airlines
Wed, Sep 24 - Sat, Sep 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 4 days ago
$130
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Sep 24 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $130 found 4 days ago
Frontier Airlines
Tue, Jul 15 - Wed, Jul 23
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Jul 15 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Jul 23, priced at $139 found 4 days ago
American Airlines
Tue, Sep 9 - Tue, Sep 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 10 hours ago
$152
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Sep 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $152 found 10 hours ago
United
Mon, Aug 25 - Thu, Aug 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 8 hours ago
$157
Roundtrip
found 8 hours ago
Select United flight, departing Mon, Aug 25 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $157 found 8 hours ago
Contour Airlines
Mon, Sep 8 - Thu, Sep 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Mon, Sep 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $189 found 1 day ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 10 hours ago
$191
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $191 found 10 hours ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 19 hours ago
$197
Roundtrip
found 19 hours ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 19 hours ago
Alaska Airlines
Tue, Oct 14 - Tue, Oct 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 11 hours ago
$216
Roundtrip
found 11 hours ago
Select Alaska Airlines flight, departing Tue, Oct 14 from Los Angeles Intl. to O'Hare Intl., returning Tue, Oct 28, priced at $216 found 11 hours ago
Delta
Mon, Aug 11 - Tue, Aug 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$255 Roundtrip, found 6 hours ago
$255
Roundtrip
found 6 hours ago
Select Delta flight, departing Mon, Aug 11 from Los Angeles Intl. to Midway Intl., returning Tue, Aug 12, priced at $255 found 6 hours ago
Frontier Airlines
Fri, Jul 11 - Sat, Jul 12
ONT
Los Angeles - Ontario Intl.
MDW
Midway Intl.
$279 Roundtrip, found 2 days ago
$279
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jul 11 from Los Angeles - Ontario Intl. to Midway Intl., returning Sat, Jul 12, priced at $279 found 2 days ago
Frontier Airlines
Sat, Jul 26 - Sun, Jul 27
ONT
Los Angeles - Ontario Intl.
ORD
O'Hare Intl.
$282 Roundtrip, found 5 days ago
$282
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Jul 26 from Los Angeles - Ontario Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $282 found 5 days ago
JetBlue Airways
Tue, Oct 14 - Tue, Oct 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$291 Roundtrip, found 11 hours ago
$291
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Oct 14 from Los Angeles Intl. to O'Hare Intl., returning Tue, Oct 28, priced at $291 found 11 hours ago
Hawaiian Airlines
Tue, Jul 22 - Tue, Jul 29
ONT
Los Angeles - Ontario Intl.
ORD
O'Hare Intl.
$334 Roundtrip, found 5 days ago
$334
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Tue, Jul 22 from Los Angeles - Ontario Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $334 found 5 days ago
Sun Country Airlines
Mon, Jul 21 - Mon, Jul 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$358 Roundtrip, found 21 hours ago
$358
Roundtrip
found 21 hours ago
Select Sun Country Airlines flight, departing Mon, Jul 21 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jul 28, priced at $358 found 21 hours ago

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 July, 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 $112, 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 $112 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$75

Last Minute Hotel Deals in Hillside

InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (1,970 reviews)
"Even after renovation rooms are still looking dated"

Reviewed on Jul 4, 2025

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InterContinental Chicago Magnificent Mile by IHG
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
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! (8,872 reviews)
"The history of the hotel is amazing and she might be an old girl with old features but she still shines like a diamond. Plus, the lake side view cannot be beat."

Reviewed on Jul 4, 2025

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Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,372 reviews)
"Very nice hotel! No pool though it was out of service"

Reviewed on Jul 3, 2025

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Hilton Chicago/Magnificent Mile Suites
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
4 out of 5
O'Hare International Airport, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8/10 Very Good! (2,049 reviews)
"Convenient to airport after flight got cancelled not once but twice ."

Reviewed on Jul 2, 2025

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Hilton Chicago O'Hare Airport
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
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,357 reviews)
"The location is very convenient, close to the train and easy to get to most attractions. The rokms are spacious and clean. The breakfast and happy hour are very good and a nice convenience."

Reviewed on Jul 5, 2025

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Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
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! (3,284 reviews)
"Very nice stay. Looking forward to be back."

Reviewed on Jul 5, 2025

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citizenM Chicago Downtown
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 out of 5
105 E Delaware Pl, Chicago, IL
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
8.2/10 Very Good! (3,458 reviews)
"Good"

Reviewed on Jul 3, 2025

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The Whitehall Hotel, BW Premier Collection
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
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 ...
8/10 Very Good! (1,823 reviews)
Loved this hotel!
"This hotel was just perfect! The staff were all very friendly, especially service desk. The rooms were well stocked. The room was a bit small, but it didn't bother us. Within walking distance to everything! Will definitely be staying here again. Thank you for a great experience ❤️"

Reviewed on Jul 2, 2025

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Hotel Felix River North/Magnificent Mile
See all 4,955 properties in Hillside
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
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! (1,002 reviews)
"It was great for the price they were remodeling some things"

Reviewed on Jul 5, 2025

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Best Western Plus Chicago Hillside
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
2.5 out of 5
200 S Mannheim Road, Hillside, IL
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 (1,006 reviews)
"Nice staff very friendly and helpful. Room was nice. Pool area clean and tidy. Excellent breakfast"

Reviewed on Jul 3, 2025

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Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 4,955 properties in Hillside
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.