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Hillside

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Hillside Flights as Low as $96

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

Frontier Airlines
Fri, Jul 4 - Mon, Jul 7
BNA
Nashville Intl.
ORD
O'Hare Intl.
$96 Roundtrip, found 6 hours ago
$96
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, Jul 4 from Nashville Intl. to O'Hare Intl., returning Mon, Jul 7, priced at $96 found 6 hours ago
Frontier Airlines
Fri, Jul 4 - Mon, Jul 7
BNA
Nashville Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 6 hours ago
$98
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, Jul 4 from Nashville Intl. to O'Hare Intl., returning Mon, Jul 7, priced at $98 found 6 hours ago
Spirit Airlines
Fri, Jun 6 - Mon, Jun 9
BNA
Nashville Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 6 hours ago
$100
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Fri, Jun 6 from Nashville Intl. to O'Hare Intl., returning Mon, Jun 9, priced at $100 found 6 hours ago
Spirit Airlines
Fri, May 30 - Wed, Jun 4
BNA
Nashville Intl.
ORD
O'Hare Intl.
$105 Roundtrip, found 2 days ago
$105
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Fri, May 30 from Nashville Intl. to O'Hare Intl., returning Wed, Jun 4, priced at $105 found 2 days ago
Frontier Airlines
Sat, May 24 - Sat, Jun 14
DEN
Denver Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 8 hours ago
$109
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Denver Intl. to O'Hare Intl., returning Sat, Jun 14, priced at $109 found 8 hours ago
United
Fri, Jul 4 - Mon, Jul 7
BNA
Nashville Intl.
ORD
O'Hare Intl.
$145 Roundtrip, found 6 hours ago
$145
Roundtrip
found 6 hours ago
Select United flight, departing Fri, Jul 4 from Nashville Intl. to O'Hare Intl., returning Mon, Jul 7, priced at $145 found 6 hours ago
American Airlines
Fri, Jul 4 - Mon, Jul 7
BNA
Nashville Intl.
ORD
O'Hare Intl.
$145 Roundtrip, found 6 hours ago
$145
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Fri, Jul 4 from Nashville Intl. to O'Hare Intl., returning Mon, Jul 7, priced at $145 found 6 hours ago
Bargain Flight
Sat, May 17 - Mon, May 19
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, May 17 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Mon, May 19, priced at $163 found 1 day ago
Bargain Flight
Thu, May 8 - Thu, May 15
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$167 Roundtrip, found 12 hours ago
$167
Roundtrip
found 12 hours ago
Select Bargain Flight flight, departing Thu, May 8 from Ronald Reagan Washington National to O'Hare Intl., returning Thu, May 15, priced at $167 found 12 hours ago
Frontier Airlines
Sat, Jul 19 - Sat, Jul 26
DEN
Denver Intl.
MDW
Midway Intl.
$168 Roundtrip, found 4 days ago
$168
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jul 19 from Denver Intl. to Midway Intl., returning Sat, Jul 26, priced at $168 found 4 days ago
Delta
Sat, Jul 5 - Sat, Jul 5
BNA
Nashville Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 6 hours ago
$171
Roundtrip
found 6 hours ago
Select Delta flight, departing Sat, Jul 5 from Nashville Intl. to O'Hare Intl., returning Sat, Jul 5, priced at $171 found 6 hours ago
JetBlue Airways
Tue, Jun 3 - Wed, Jun 11
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$205 Roundtrip, found 4 days ago
$205
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Jun 3 from Ronald Reagan Washington National to O'Hare Intl., returning Wed, Jun 11, priced at $205 found 4 days ago
Frontier Airlines
Mon, May 5 - Mon, May 5
CVG
Cincinnati - Northern Kentucky Intl.
MDW
Midway Intl.
$296 Roundtrip, found 3 days ago
$296
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, May 5 from Cincinnati - Northern Kentucky Intl. to Midway Intl., returning Mon, May 5, priced at $296 found 3 days ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Jun 16 - Sat, Jun 21
DEN
Denver Intl.
ORD
O'Hare Intl.
$342 Roundtrip, found 4 days ago
$342
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Jun 16 from Denver Intl. to O'Hare Intl., returning Sat, Jun 21, priced at $342 found 4 days ago
Delta
Sun, May 4 - Wed, May 7
DCA
Ronald Reagan Washington National
MDW
Midway Intl.
$559 Roundtrip, found 2 days ago
$559
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, May 4 from Ronald Reagan Washington National to Midway Intl., returning Wed, May 7, priced at $559 found 2 days ago
Alaska Airlines
Fri, May 16 - Mon, May 19
CVG
Cincinnati - Northern Kentucky Intl.
ORD
O'Hare Intl.
$5,690 Roundtrip, found 4 hours ago
$5,690
Roundtrip
found 4 hours ago
Select Alaska Airlines flight, departing Fri, May 16 from Cincinnati - Northern Kentucky Intl. to O'Hare Intl., returning Mon, May 19, priced at $5,690 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 July, 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 14 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 $96, 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 $96 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$96

Last Minute Hotel Deals in Hillside

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 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,959 reviews)
"Parking is expensive and not recommended on property due to $70 charge. $50 around corner. Besides that hotel was perfect. Pool is smaller, breakfast is great. And the staff was great at handling the large crowds!"

Reviewed on Apr 30, 2025

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Embassy Suites by Hilton Chicago Downtown River North
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! (8,730 reviews)
"My stay was good! I did not like that breakfast was so expensive for hotel guests but the stay was good nonetheless."

Reviewed on May 1, 2025

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Congress Plaza 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 ...
8.8/10 Excellent! (2,167 reviews)
"Everything excellent just in our room we struggled with hot water… but everything ok"

Reviewed on Apr 28, 2025

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Hilton Chicago/Magnificent Mile Suites
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
8.8/10 Excellent! (2,075 reviews)
"Stayed at Swissotel but very close to Hyatt Regency Chicago (0.2 miles) where my meeting was held."

Reviewed on Apr 30, 2025

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Swissotel - Chicago
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! (4,101 reviews)
"Thus property was beautiful, very clean, friendly staff and there was free coffee. Amazing views made it even better. We walked across the street to the River Walk and down the block to a boat tour. We also walked to a bar and a restaurant downtown. If we go back to Chicago, we would definitely stay ..."

Reviewed on Apr 27, 2025

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River Hotel
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,021 reviews)
"Great stay."

Reviewed on Apr 28, 2025

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Crowne Plaza Chicago West Loop by IHG
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! (2,988 reviews)
Small but great vibe
"Great common areas. Very tiny rooms but if you don’t plan on being in the room much the rest of the place is worth it. Great breakfast options, limited food rest of day."

Reviewed on Apr 28, 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! (1,686 reviews)
"-"

Reviewed on Apr 29, 2025

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Fairmont Chicago at Millennium Park
See all 4,628 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
The price is $93 per night from May 6 to May 7
$93
includes taxes & fees
May 6 - May 7
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)
Convenient
"Convenient in middle of Illinois, not a lot of options."

Reviewed on Apr 9, 2025

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
The price is $94 per night from May 11 to May 12
$94
includes taxes & fees
May 11 - May 12
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 (1,010 reviews)
"Super friendly"

Reviewed on Apr 28, 2025

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 4,628 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.