Search Cheap Flights to
Hillside

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Hillside Flights as Low as $97

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

JetBlue Airways
Tue, May 13 - Tue, May 20
BOS
Logan Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 4 days ago
$97
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, May 13 from Logan Intl. to O'Hare Intl., returning Tue, May 20, priced at $97 found 4 days ago
United
Wed, Apr 2 - Mon, Apr 7
BOS
Logan Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 11 hours ago
$97
Roundtrip
found 11 hours ago
Select United flight, departing Wed, Apr 2 from Logan Intl. to O'Hare Intl., returning Mon, Apr 7, priced at $97 found 11 hours ago
Delta
Wed, Jun 25 - Sat, Jun 28
BOS
Logan Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 25 from Logan Intl. to O'Hare Intl., returning Sat, Jun 28, priced at $97 found 2 days ago
Spirit Airlines
Thu, Apr 3 - Mon, Apr 7
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Apr 3 from George Bush Intercontinental to O'Hare Intl., returning Mon, Apr 7, priced at $98 found 2 days ago
Frontier Airlines
Thu, Apr 3 - Tue, Apr 8
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$99 Roundtrip, found 6 days ago
$99
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Apr 3 from George Bush Intercontinental to O'Hare Intl., returning Tue, Apr 8, priced at $99 found 6 days ago
Spirit Airlines
Thu, Apr 10 - Sat, Apr 12
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$100 Roundtrip, found 10 hours ago
$100
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Thu, Apr 10 from George Bush Intercontinental to O'Hare Intl., returning Sat, Apr 12, priced at $100 found 10 hours ago
United
Tue, Aug 19 - Sat, Aug 23
BOS
Logan Intl.
ORD
O'Hare Intl.
$103 Roundtrip, found 2 days ago
$103
Roundtrip
found 2 days ago
Select United flight, departing Tue, Aug 19 from Logan Intl. to O'Hare Intl., returning Sat, Aug 23, priced at $103 found 2 days ago
United
Tue, Aug 19 - Sat, Aug 23
BOS
Logan Intl.
ORD
O'Hare Intl.
$104 Roundtrip, found 2 days ago
$104
Roundtrip
found 2 days ago
Select United flight, departing Tue, Aug 19 from Logan Intl. to O'Hare Intl., returning Sat, Aug 23, priced at $104 found 2 days ago
Frontier Airlines
Wed, Jun 11 - Wed, Jun 18
IAH
George Bush Intercontinental
MDW
Midway Intl.
$104 Roundtrip, found 5 days ago
$104
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Jun 11 from George Bush Intercontinental to Midway Intl., returning Wed, Jun 18, priced at $104 found 5 days ago
Spirit Airlines
Wed, Apr 2 - Mon, Apr 7
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$108 Roundtrip, found 6 days ago
$108
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Apr 2 from George Bush Intercontinental to O'Hare Intl., returning Mon, Apr 7, priced at $108 found 6 days ago
Frontier Airlines
Mon, Jun 16 - Wed, Jun 18
IAH
George Bush Intercontinental
MDW
Midway Intl.
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Jun 16 from George Bush Intercontinental to Midway Intl., returning Wed, Jun 18, priced at $108 found 5 days ago
Frontier Airlines
Wed, May 28 - Fri, May 30
AUS
Austin-Bergstrom Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 4 days ago
$130
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, May 28 from Austin-Bergstrom Intl. to O'Hare Intl., returning Fri, May 30, priced at $130 found 4 days ago
JetBlue Airways
Sat, May 24 - Wed, May 28
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 1 day ago
$135
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, May 24 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, May 28, priced at $135 found 1 day ago
American Airlines
Wed, Apr 2 - Mon, Apr 7
BOS
Logan Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 11 hours ago
$137
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Apr 2 from Logan Intl. to O'Hare Intl., returning Mon, Apr 7, priced at $137 found 11 hours ago
Frontier Airlines
Thu, May 15 - Mon, May 19
BOS
Logan Intl.
MDW
Midway Intl.
$195 Roundtrip, found 5 days ago
$195
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, May 15 from Logan Intl. to Midway Intl., returning Mon, May 19, priced at $195 found 5 days ago
Delta
Thu, Apr 24 - Thu, May 1
AUS
Austin-Bergstrom Intl.
MDW
Midway Intl.
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Apr 24 from Austin-Bergstrom Intl. to Midway Intl., returning Thu, May 1, priced at $217 found 3 days 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 $97, 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 $97 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$97

Last Minute Hotel Deals in Hillside

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $128 per night from Mar 23 to Mar 24
$128
includes taxes & fees
Mar 23 - Mar 24
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! (3,934 reviews)
"Very nice and clean."

Reviewed on Mar 20, 2025

River Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
The price is $193 per night from Mar 23 to Mar 24
$193
includes taxes & fees
Mar 23 - Mar 24
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and ...
9.6/10 Exceptional! (1,907 reviews)
"Staff was welcoming and very helpful"

Reviewed on Mar 20, 2025

L7 Chicago by LOTTE
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is $164 per night from Apr 20 to Apr 21
$164
includes taxes & fees
Apr 20 - Apr 21
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! (1,001 reviews)
"Friendly staff and spacious room. Easy check-in"

Reviewed on Mar 17, 2025

The Westin Michigan Avenue Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $157 per night from Mar 22 to Mar 23
$157
includes taxes & fees
Mar 22 - Mar 23
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! (8,594 reviews)
"Hotel is older- has some character. Rooms are basic but clean. No frills. Great location."

Reviewed on Mar 20, 2025

Congress Plaza 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
The price is $117 per night from Mar 27 to Mar 28
$117
includes taxes & fees
Mar 27 - Mar 28
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 ...
8.6/10 Excellent! (1,004 reviews)
"We really enjoyed staying here. The parking was easy to get to. The staff was very nice and helpful. The lobby is very nice and cozy. It just seems to be an older hotel, so with age some of the fixtures/decor were out dated. That wasn't a problem for me, but it could be for some! It's in a nice area ..."

Reviewed on Mar 17, 2025

Crowne Plaza Chicago West Loop by IHG
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3 out of 5
10 E Grand Ave, Chicago, IL
The price is $126 per night from Apr 6 to Apr 7
$126
includes taxes & fees
Apr 6 - Apr 7
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (3,090 reviews)
"Nice hotel with pleasant, helpful, professional staff. I always enjoy staying there!"

Reviewed on Mar 20, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
The price is $131 per night from Mar 26 to Mar 27
$131
includes taxes & fees
Mar 26 - Mar 27
Book a stay at this eco-certified hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,408 reviews)
"Easy check in. Clean property. Clean room. Great quick stay."

Reviewed on Mar 21, 2025

Hyatt Regency O'Hare Chicago
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is $224 per night from Mar 23 to Mar 24
$224
includes taxes & fees
Mar 23 - Mar 24
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! (1,967 reviews)
"Great"

Reviewed on Mar 20, 2025

Swissotel - Chicago
See all 4,626 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 $98 per night from Mar 25 to Mar 26
$98
includes taxes & fees
Mar 25 - Mar 26
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)
"The front desk was very polite and helpful, rooms were very clean and the bar was fantastic as always"

Reviewed on Mar 6, 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 $90 per night from Apr 17 to Apr 18
$90
includes taxes & fees
Apr 17 - Apr 18
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 (1,000 reviews)
"Was easy to check in, friendly"

Reviewed on Mar 10, 2025

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 4,626 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.