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Hillside

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Hillside Flights as Low as $111

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

Frontier Airlines
Tue, Aug 11 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$111 Roundtrip, found 19 hours ago
$111
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $111 found 19 hours ago
Frontier Airlines
Wed, Oct 21 - Tue, Nov 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 19 hours ago
$138
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Nov 10, priced at $138 found 19 hours ago
Frontier Airlines
Wed, Sep 2 - Wed, Sep 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 6 hours ago
$148
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $148 found 6 hours ago
Frontier Airlines
Sat, Sep 26 - Sat, Oct 3
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$148 Roundtrip, found 2 days ago
$148
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, Oct 3, priced at $148 found 2 days ago
Frontier Airlines
Tue, Aug 11 - Thu, Aug 20
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$167 Roundtrip, found 6 hours ago
$167
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Dallas-Fort Worth Intl. to Midway Intl., returning Thu, Aug 20, priced at $167 found 6 hours ago
Bargain Flight
Mon, Jul 20 - Fri, Jul 24
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Mon, Jul 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Fri, Jul 24, priced at $174 found 2 days ago
American Airlines
Wed, Sep 9 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Sep 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $192 found 1 day ago
Delta
Wed, Sep 9 - Wed, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $192 found 1 day ago
Frontier Airlines
Wed, Aug 26 - Tue, Sep 1
AUS
Austin-Bergstrom Intl.
ORD
O'Hare Intl.
$210 Roundtrip, found 4 days ago
$210
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Austin-Bergstrom Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $210 found 4 days ago
Frontier Airlines
Wed, Aug 5 - Tue, Aug 18
IAH
George Bush Intercontinental
MDW
Midway Intl.
$215 Roundtrip, found 5 hours ago
$215
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Aug 5 from George Bush Intercontinental to Midway Intl., returning Tue, Aug 18, priced at $215 found 5 hours ago
Frontier Airlines
Tue, Nov 10 - Tue, Nov 17
AUS
Austin-Bergstrom Intl.
MDW
Midway Intl.
$244 Roundtrip, found 4 days ago
$244
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Nov 10 from Austin-Bergstrom Intl. to Midway Intl., returning Tue, Nov 17, priced at $244 found 4 days ago
JetBlue Airways
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$279 Roundtrip, found 11 hours ago
$279
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $279 found 11 hours ago
Delta
Sat, Aug 8 - Tue, Aug 11
DAL
Love Field
MDW
Midway Intl.
$285 Roundtrip, found 1 day ago
$285
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 8 from Love Field to Midway Intl., returning Tue, Aug 11, priced at $285 found 1 day ago
American Airlines
Fri, Jul 24 - Fri, Jul 31
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$285 Roundtrip, found 11 hours ago
$285
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Jul 24 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, Jul 31, priced at $285 found 11 hours ago
Contour Airlines
Tue, Sep 1 - Wed, Sep 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$289 Roundtrip, found 6 hours ago
$289
Roundtrip
found 6 hours ago
Select Contour Airlines flight, departing Tue, Sep 1 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $289 found 6 hours ago
Delta
Wed, Sep 2 - Wed, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$291 Roundtrip, found 6 hours ago
$291
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Sep 2 from Love Field to O'Hare Intl., returning Wed, Sep 9, priced at $291 found 6 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 August, 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 $111, 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 $111 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$110

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! (10,176 reviews)
"In the 1980s and 1990s, I often stayed at this hotel when I went to Chicago for conferences or events at the Art Institute of Chicago. The location is still great for getting to the Art Institute (easy walking distance). Sadly, the hotel has become shabby. The bathroom in my unit appeared to have ..."

Reviewed on Jun 30, 2026

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Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,821 reviews)
"Quiet room, with plenty of space to relax. Great location on the Mag Mile. Breakfast cost was very high and there are other smaller neighborhood breakfast spots to go to. Bar/lounge was great. Did not eat there for dinner but menu looked good."

Reviewed on Jun 30, 2026

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Omni Chicago 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 ...
9/10 Wonderful! (4,488 reviews)
"The shower was awful. The curtain wouldn’t fully close on either end due to the rod slanting upwards which led to water getting everywhere on the floor. The water pressure was also terrible and"

Reviewed on Jun 30, 2026

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Hilton Chicago/Magnificent Mile Suites
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 ...
8.8/10 Excellent! (2,756 reviews)
"They over charge your card and then can’t tell what the charge is for or make something up. When we got there they gave us a dirty room and we had to call to get out room changed not a upgrade but whatever."

Reviewed on Jun 30, 2026

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Hyatt Regency O'Hare Chicago
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,586 reviews)
"EXCELLENT , BREAKFAST AREA IS VERY GOOD AND THE JOURNEY IS AMAZING. ROOMS ARE COMPLETELY NEAT AND CONFORTABLE .HOTEL IS VERY WELL LOCATED ."

Reviewed on Jun 30, 2026

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Hotel Riu Plaza Chicago
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! (2,331 reviews)
"Staff were really helpful and sweet during check in. During checkout I was told there are no shuttles to take me to my terminal in quite a short and ubrupt manner. But to be honest the price is ridiculous for the outdated hotel. Seems like they think they can charge Hilton prices for what looks like ..."

Reviewed on Jun 30, 2026

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Hilton Chicago O'Hare Airport
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! (5,281 reviews)
"Beautiful hotel; excellent location; rooms a little small but reasonable."

Reviewed on Jun 30, 2026

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River Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,668 reviews)
"Hotel and staff were amazing Cable and internet down the whole time Breakfast not great"

Reviewed on Jun 30, 2026

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The Chicago Hotel Collection - Magnificent Mile
See all 4,879 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 ...
7.6/10 Good! (1,007 reviews)
"Property was decent. Only one elevator working and it sounded like it was about ready to break down. The pool was not open and this location did not offer a complimentary breakfast, usually one of the reasons I choose BW's. So disappointed in this location."

Reviewed on Jun 26, 2026

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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 ...
7.2/10 Good! (1,006 reviews)
"We wish to provide detailed feedback regarding a significant operational challenge encountered during our recent stay, which considerably impacted our experience. Upon arrival, we observed a considerable queue and extended waiting periods for the single operational elevator, indicating the strain ..."

Reviewed on Jun 28, 2026

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Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 4,879 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.