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Hillside

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Hillside Flights as Low as $72

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

Frontier Airlines
Wed, May 6 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 7 hours ago
$72
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 12, priced at $72 found 7 hours ago
Frontier Airlines
Tue, Apr 28 - Tue, May 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$88 Roundtrip, found 2 hours ago
$88
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, May 5, priced at $88 found 2 hours ago
Spirit Airlines
Wed, May 6 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 7 hours ago
$97
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Wed, May 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 12, priced at $97 found 7 hours ago
Frontier Airlines
Fri, Apr 17 - Sat, Apr 25
TPA
Tampa Intl.
ORD
O'Hare Intl.
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Apr 17 from Tampa Intl. to O'Hare Intl., returning Sat, Apr 25, priced at $121 found 1 day ago
Spirit Airlines
Wed, Apr 22 - Tue, May 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$123 Roundtrip, found 1 hour ago
$123
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Apr 22 from Los Angeles Intl. to O'Hare Intl., returning Tue, May 5, priced at $123 found 1 hour ago
Frontier Airlines
Wed, Apr 15 - Wed, Apr 29
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$144 Roundtrip, found 16 hours ago
$144
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Wed, Apr 15 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Wed, Apr 29, priced at $144 found 16 hours ago
Frontier Airlines
Wed, Apr 22 - Tue, Apr 28
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$150 Roundtrip, found 1 day ago
$150
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Tue, Apr 28, priced at $150 found 1 day ago
Frontier Airlines
Wed, May 13 - Sat, May 16
TPA
Tampa Intl.
MDW
Midway Intl.
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, May 13 from Tampa Intl. to Midway Intl., returning Sat, May 16, priced at $163 found 2 days ago
Bargain Flight
Sun, May 17 - Tue, May 19
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Sun, May 17 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Tue, May 19, priced at $179 found 5 days ago
Delta
Tue, Apr 14 - Sat, Apr 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$196 Roundtrip, found 3 hours ago
$196
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Apr 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Apr 25, priced at $196 found 3 hours ago
Frontier Airlines
Thu, Apr 9 - Tue, Apr 14
LAX
Los Angeles Intl.
MDW
Midway Intl.
$212 Roundtrip, found 3 hours ago
$212
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Los Angeles Intl. to Midway Intl., returning Tue, Apr 14, priced at $212 found 3 hours ago
American Airlines
Tue, May 26 - Tue, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
RFD
Greater Rockford
$222 Roundtrip, found 5 days ago
$222
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, May 26 from Baltimore Washington Intl. Thurgood Marshall to Greater Rockford, returning Tue, Jun 2, priced at $222 found 5 days ago
American Airlines
Thu, May 14 - Mon, May 18
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$267 Roundtrip, found 1 day ago
$267
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, May 14 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Mon, May 18, priced at $267 found 1 day ago
Sun Country Airlines
Thu, Apr 9 - Sun, Apr 12
PIE
St. Petersburg-Clearwater Intl.
ORD
O'Hare Intl.
$469 Roundtrip, found 6 hours ago
$469
Roundtrip
found 6 hours ago
Select Sun Country Airlines flight, departing Thu, Apr 9 from St. Petersburg-Clearwater Intl. to O'Hare Intl., returning Sun, Apr 12, priced at $469 found 6 hours ago
American Airlines
Fri, Jul 31 - Sun, Aug 2
TPA
Tampa Intl.
RFD
Greater Rockford
$495 Roundtrip, found 17 hours ago
$495
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Fri, Jul 31 from Tampa Intl. to Greater Rockford, returning Sun, Aug 2, priced at $495 found 17 hours ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$532 Roundtrip, found 4 hours ago
$532
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $532 found 4 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 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 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 $72, 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 $72 right now, why wait?

Hillside Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$67

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! (10,006 reviews)
I always stay at the Congress Hotel when I participate in the Shamrock Shuffle. This was my sixth time. This year's experience was the best. The check in was clear, concise, and professional. The room I stayed in was recently updated.

Reviewed on Mar 24, 2026

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Congress Plaza 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! (3,615 reviews)
Nice front desk staff, great breakfast

Reviewed on Mar 24, 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! (5,783 reviews)
I liked this hotel

Reviewed on Mar 24, 2026

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Embassy Suites by Hilton Chicago Downtown River North
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! (3,974 reviews)
Fast check in, the room was cleaned every day.

Reviewed on Mar 23, 2026

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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
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! (2,233 reviews)
Clean room and friendly staff

Reviewed on Mar 21, 2026

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Hilton Chicago O'Hare Airport
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (3,156 reviews)
Bathroom was dirty, there was dry pee in the toilet

Reviewed on Mar 24, 2026

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Aloft Chicago Mag Mile
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,756 reviews)
The entire hotel was a 10/10. Would definitely recommend. Also the bartender KERRY in the restaurant of the hotel was perfect, very nice, personable, and made our stay even better!!!

Reviewed on Mar 23, 2026

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The Wade
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (3,464 reviews)
So so

Reviewed on Mar 23, 2026

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Hyatt Regency Chicago
See all 5,089 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! (1,002 reviews)
Everything was good. Bathroom sink was blocked i didn’t told the staff cuz i was there for very short period of time.

Reviewed on Mar 19, 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! (1,007 reviews)
Great location, stores at walking distance and restaurants too. 20 min from the Airport!

Reviewed on Mar 23, 2026

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Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 5,089 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.