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Hillside

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Hillside Flights as Low as $56

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

Frontier Airlines
Wed, Aug 12 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$56 Roundtrip, found 6 hours ago
$56
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $56 found 6 hours ago
Frontier Airlines
Tue, Jun 9 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$66 Roundtrip, found 9 hours ago
$66
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 16, priced at $66 found 9 hours ago
Frontier Airlines
Tue, Jun 9 - Wed, Jun 17
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$76 Roundtrip, found 1 hour ago
$76
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Jun 17, priced at $76 found 1 hour ago
Frontier Airlines
Wed, May 27 - Fri, May 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$131 Roundtrip, found 1 day ago
$131
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 27 from Los Angeles Intl. to O'Hare Intl., returning Fri, May 29, priced at $131 found 1 day ago
Spirit Airlines
Sat, Aug 8 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Aug 8 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $169 found 2 days ago
United
Wed, Aug 12 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$169 Roundtrip, found 6 hours ago
$169
Roundtrip
found 6 hours ago
Select United flight, departing Wed, Aug 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $169 found 6 hours ago
American Airlines
Wed, Aug 12 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$169 Roundtrip, found 6 hours ago
$169
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Aug 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $169 found 6 hours ago
Delta
Wed, Aug 12 - Tue, Aug 18
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$197 Roundtrip, found 6 hours ago
$197
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Aug 12 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 18, priced at $197 found 6 hours ago
Delta
Tue, Sep 29 - Tue, Oct 6
IAH
George Bush Intercontinental
MDW
Midway Intl.
$207 Roundtrip, found 23 hours ago
$207
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Sep 29 from George Bush Intercontinental to Midway Intl., returning Tue, Oct 6, priced at $207 found 23 hours ago
Delta
Tue, Jun 9 - Wed, Jun 10
LAX
Los Angeles Intl.
MDW
Midway Intl.
$224 Roundtrip, just found
$224
Roundtrip
just found
Select Delta flight, departing Tue, Jun 9 from Los Angeles Intl. to Midway Intl., returning Wed, Jun 10, priced at $224 just found
Delta
Wed, Aug 26 - Tue, Sep 1
DAL
Love Field
ORD
O'Hare Intl.
$301 Roundtrip, found 12 hours ago
$301
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, Aug 26 from Love Field to O'Hare Intl., returning Tue, Sep 1, priced at $301 found 12 hours ago
Delta
Tue, Jun 2 - Sat, Jun 6
DAL
Love Field
MDW
Midway Intl.
$308 Roundtrip, found 6 days ago
$308
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jun 2 from Love Field to Midway Intl., returning Sat, Jun 6, priced at $308 found 6 days ago
Alaska Airlines
Fri, May 29 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$314 Roundtrip, found 4 hours ago
$314
Roundtrip
found 4 hours ago
Select Alaska Airlines flight, departing Fri, May 29 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $314 found 4 hours ago
American Airlines
Thu, Jun 4 - Mon, Jun 8
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jun 4 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Mon, Jun 8, priced at $317 found 1 day ago
American Airlines
Fri, May 29 - Sat, Aug 1
IAH
George Bush Intercontinental
RFD
Greater Rockford
$318 Roundtrip, found 8 hours ago
$318
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, May 29 from George Bush Intercontinental to Greater Rockford, returning Sat, Aug 1, priced at $318 found 8 hours ago
American Airlines
Sun, May 24 - Sun, May 31
LAX
Los Angeles Intl.
RFD
Greater Rockford
$403 Roundtrip, found 1 day ago
$403
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, May 24 from Los Angeles Intl. to Greater Rockford, returning Sun, May 31, priced at $403 found 1 day 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 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 $56, 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 $56 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$56

Last Minute Hotel Deals in Hillside

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (2,697 reviews)
great location

Reviewed on May 9, 2026

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Hotel Felix River North/Magnificent Mile
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! (10,191 reviews)
Rude, staffs, not responding to house service/room service. Poor service, flush kept on leaking. Very very terrible condition of the room.

Reviewed on May 9, 2026

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Congress Plaza Hotel
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! (5,188 reviews)
excellent stay

Reviewed on May 9, 2026

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River Hotel
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! (4,096 reviews)
Clean room and close to vicinity.

Reviewed on May 9, 2026

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Hotel Riu Plaza Chicago
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 hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,937 reviews)
Yes

Reviewed on May 5, 2026

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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
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (3,501 reviews)
The staff was fantastic! While the hotel shows its age, it offers good value for the price. The professionalism and extra effort from the staff compensate for the limited amenities. It’s situated in a great location.

Reviewed on May 9, 2026

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Club Quarters Hotel, Central Loop, Chicago
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! (4,281 reviews)
Nice convenient location and lots of space to spread out

Reviewed on May 8, 2026

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Hilton Chicago/Magnificent Mile Suites
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (2,299 reviews)
The Holiday Inn Voco at Wolf Point continues to exceed expectations! Warm, welcoming staff, spotless rooms and outstanding service by housekeeping! I call it my home away from home and I stay there frequently when visiting our children! Spectacular views, inviting atmosphere and stay second to none! ...

Reviewed on May 4, 2026

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Holiday Inn Chicago Dwtn - The Mart by IHG
See all 5,158 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! (1,006 reviews)
Excellent facilities, ideal and safe parking.

Reviewed on May 6, 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 ...
7/10 Good! (1,003 reviews)
The beds were NOT comfortable.

Reviewed on May 7, 2026

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Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 5,158 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.