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Hillside

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Hillside Flights as Low as $82

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

Frontier Airlines
Tue, Sep 29 - Wed, Oct 14
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Sep 29 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Wed, Oct 14, priced at $82 found 1 day ago
Frontier Airlines
Thu, Oct 22 - Mon, Oct 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 4 days ago
$118
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Los Angeles Intl. to O'Hare Intl., returning Mon, Oct 26, priced at $118 found 4 days ago
Frontier Airlines
Sat, Sep 5 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 17 hours ago
$154
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $154 found 17 hours ago
Frontier Airlines
Sat, Sep 5 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 9, priced at $165 found 1 day ago
Bargain Flight
Mon, Sep 14 - Sat, Sep 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$170 Roundtrip, found 4 days ago
$170
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Mon, Sep 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 19, priced at $170 found 4 days ago
Frontier Airlines
Wed, Sep 16 - Thu, Sep 17
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$171 Roundtrip, found 6 days ago
$171
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Newark Liberty Intl. Airport to O'Hare Intl., returning Thu, Sep 17, priced at $171 found 6 days ago
JetBlue Airways
Tue, Sep 29 - Wed, Oct 14
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 29 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Wed, Oct 14, priced at $171 found 1 day ago
American Airlines
Tue, Sep 29 - Wed, Oct 14
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 29 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Wed, Oct 14, priced at $171 found 1 day ago
Frontier Airlines
Wed, Sep 23 - Sat, Oct 10
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$177 Roundtrip, found 9 hours ago
$177
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Sep 23 from Fort Lauderdale - Hollywood Intl. to Midway Intl., returning Sat, Oct 10, priced at $177 found 9 hours ago
Delta
Fri, Nov 6 - Mon, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 18 hours ago
$197
Roundtrip
found 18 hours ago
Select Delta flight, departing Fri, Nov 6 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $197 found 18 hours ago
Southwest Airlines
Sat, Sep 26 - Wed, Sep 30
LAX
Los Angeles Intl.
MDW
Midway Intl.
$210 Roundtrip, found 15 hours ago
$210
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Sat, Sep 26 from Los Angeles Intl. to Midway Intl., returning Wed, Sep 30, priced at $210 found 15 hours ago
Frontier Airlines
Wed, Aug 26 - Tue, Sep 1
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$211 Roundtrip, found 6 days ago
$211
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Sep 1, priced at $211 found 6 days ago
Alaska Airlines
Sat, Nov 14 - Tue, Nov 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$317 Roundtrip, found 20 hours ago
$317
Roundtrip
found 20 hours ago
Select Alaska Airlines flight, departing Sat, Nov 14 from Los Angeles Intl. to O'Hare Intl., returning Tue, Nov 17, priced at $317 found 20 hours ago
American Airlines
Wed, Aug 26 - Sun, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$401 Roundtrip, found 3 days ago
$401
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Aug 26 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sun, Aug 30, priced at $401 found 3 days ago
Sun Country Airlines
Thu, Oct 22 - Mon, Oct 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$403 Roundtrip, found 4 days ago
$403
Roundtrip
found 4 days ago
Select Sun Country Airlines flight, departing Thu, Oct 22 from Los Angeles Intl. to O'Hare Intl., returning Mon, Oct 26, priced at $403 found 4 days ago
American Airlines
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$429 Roundtrip, found 20 hours ago
$429
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Tue, Sep 8, priced at $429 found 20 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 September, 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 15 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 $82, 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 $82 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$118

Last Minute Hotel Deals in Hillside

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 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,304 reviews)
"Lovely stay, beautiful architecture"

Reviewed on Aug 24, 2026

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Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
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The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,436 reviews)
"Convenient location and beautiful hotel!"

Reviewed on Aug 23, 2026

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Hilton Chicago O'Hare Airport
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
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Kasa Magnificent Mile Chicago
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,316 reviews)
"The hotel was a great location for us because it was within walking distance of our concert at Soldier Field. Parking was very easy to access. The check-in process was quick and friendly. The room was clean and spacious. The staff was professional and accommodating, especially when I needed to ask ..."

Reviewed on Aug 24, 2026

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Hyatt Regency McCormick Place Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,438 reviews)
"Green hotel and staff amenities were awesome"

Reviewed on Aug 24, 2026

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River Hotel
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
9/10 Wonderful! (2,824 reviews)
"Our room was beautiful Lynn appointed, just large enough for two people who like each other. No extras: just the bed, a desk, and locked dresser in the bedroom, and a tub/shower and sink/vanity in the bath..just roomy enough for a couple; excessively cosy if you aren’t."

Reviewed on Aug 24, 2026

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The Allegro Royal Sonesta Hotel Chicago Loop
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
9/10 Wonderful! (3,073 reviews)
"Everything was great, staff was very helpful and amenities were available. $45 for a guest parking their car is a little much"

Reviewed on Aug 24, 2026

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Hyatt Regency O'Hare Chicago
See all 5,001 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
Book a stay at this business-friendly hotel in Hillside. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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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 ...
Get rates
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 5,001 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.