Search Cheap Flights to
Hillside

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Hillside Flights as Low as $100

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

Frontier Airlines
Thu, May 29 - Sun, Jun 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Jun 1, priced at $100 found 2 days ago
Spirit Airlines
Tue, Jul 8 - Tue, Jul 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 1 hour ago
$100
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $100 found 1 hour ago
Spirit Airlines
Tue, Jun 24 - Sat, Jun 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 5 hours ago
$100
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Tue, Jun 24 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Jun 28, priced at $100 found 5 hours ago
Spirit Airlines
Wed, Jul 9 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 3 hours ago
$102
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Wed, Jul 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $102 found 3 hours ago
Frontier Airlines
Sat, Jun 14 - Sun, Jun 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$117 Roundtrip, found 7 hours ago
$117
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Jun 14 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sun, Jun 15, priced at $117 found 7 hours ago
United
Tue, Aug 19 - Tue, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 14 hours ago
$137
Roundtrip
found 14 hours ago
Select United flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $137 found 14 hours ago
Delta
Tue, Aug 19 - Tue, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 14 hours ago
$137
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $137 found 14 hours ago
American Airlines
Tue, Aug 19 - Tue, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 14 hours ago
$137
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 26, priced at $137 found 14 hours ago
Frontier Airlines
Tue, Jul 29 - Tue, Aug 5
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$178 Roundtrip, found 14 hours ago
$178
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Tue, Jul 29 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Aug 5, priced at $178 found 14 hours ago
Frontier Airlines
Mon, Jul 28 - Fri, Aug 1
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 15 hours ago
$189
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Mon, Jul 28 from Sky Harbor Intl. to O'Hare Intl., returning Fri, Aug 1, priced at $189 found 15 hours ago
Delta
Tue, Jul 15 - Tue, Jul 15
DAL
Love Field
ORD
O'Hare Intl.
$194 Roundtrip, found 5 days ago
$194
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jul 15 from Love Field to O'Hare Intl., returning Tue, Jul 15, priced at $194 found 5 days ago
Delta
Sat, Jul 5 - Tue, Jul 15
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jul 5 from Love Field to Midway Intl., returning Tue, Jul 15, priced at $197 found 2 days ago
Contour Airlines
Wed, Jul 23 - Mon, Jul 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$213 Roundtrip, just found
$213
Roundtrip
just found
Select Contour Airlines flight, departing Wed, Jul 23 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Jul 28, priced at $213 just found
Alaska Airlines
Tue, Aug 26 - Sat, Aug 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 12 hours ago
$216
Roundtrip
found 12 hours ago
Select Alaska Airlines flight, departing Tue, Aug 26 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $216 found 12 hours ago
Frontier Airlines
Thu, Aug 7 - Thu, Aug 14
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$227 Roundtrip, found 23 hours ago
$227
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Thu, Aug 7 from Sky Harbor Intl. to Midway Intl., returning Thu, Aug 14, priced at $227 found 23 hours ago
Delta
Mon, Jul 14 - Tue, Jul 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$255 Roundtrip, found 1 hour ago
$255
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Jul 14 from Los Angeles Intl. to Midway Intl., returning Tue, Jul 15, priced at $255 found 1 hour 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 May, 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 $100, 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 $100 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$100

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 free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,815 reviews)
"The hotel needs renovation"

Reviewed on May 22, 2025

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Congress Plaza Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Stay at this 4-star family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
8/10 Very Good! (2,857 reviews)
"Very nice clean hotel close to everything!"

Reviewed on May 22, 2025

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Warwick Allerton - Chicago
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold Coast
4 out of 5
1301 N State Pkwy, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.4/10 Very Good! (1,010 reviews)
"David the bartender was exceptional, with attention to detail to everything and extremely professional. Awesome bar stuff."

Reviewed on May 22, 2025

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The Chicago Hotel Collection Ambassador Gold Coast
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
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! (4,170 reviews)
Elevator an issue
"Hotel was great but our room was behind the elevator so we heard it go up and down all night. They should have let us know and the hotel should discount this room."

Reviewed on May 22, 2025

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River Hotel
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! (3,085 reviews)
"Loved everything about it. If I had to say I had a complaint it would be needing a way to charge phone near the Bed."

Reviewed on May 23, 2025

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citizenM Chicago Downtown
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 out of 5
200 North Columbus Drive, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,751 reviews)
"I loved the location of the property to park."

Reviewed on May 21, 2025

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Fairmont Chicago at Millennium Park
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! (2,255 reviews)
"Hilton is the way to go. My wife loves shopping and all the best shops are just right around the corner. Workers here are very nice and polite."

Reviewed on May 22, 2025

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Hilton Chicago/Magnificent Mile Suites
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury 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! (1,000 reviews)
"Beautiful hotel! Great area, great staff! Having a Starbucks in the hotel is extremely convenient. Parking was easy and the garage is close. I enjoyed my stay."

Reviewed on May 13, 2025

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The Westin Michigan Avenue Chicago
See all 4,672 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! (1,001 reviews)
"Comfortable"

Reviewed on May 20, 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 (1,003 reviews)
"Very clean. Room was very nice. Area is safe and clean. Staff was just very unprofessional and hid in a room."

Reviewed on May 22, 2025

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Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 4,672 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.