Search Cheap Flights to
Hillside

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Hillside Flights as Low as $108

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

Frontier Airlines
Fri, Oct 2 - Tue, Oct 6
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Oct 2 from George Bush Intercontinental to O'Hare Intl., returning Tue, Oct 6, priced at $108 found 2 days ago
Frontier Airlines
Mon, Aug 24 - Thu, Aug 27
IAH
George Bush Intercontinental
MDW
Midway Intl.
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Aug 24 from George Bush Intercontinental to Midway Intl., returning Thu, Aug 27, priced at $169 found 1 day ago
Frontier Airlines
Sat, Sep 5 - Sun, Sep 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 18 hours ago
$171
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Los Angeles Intl. to O'Hare Intl., returning Sun, Sep 6, priced at $171 found 18 hours ago
Frontier Airlines
Wed, Oct 21 - Sat, Oct 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 18 hours ago
$197
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Logan Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $197 found 18 hours ago
Bargain Flight
Fri, Oct 16 - Mon, Oct 19
BOS
Logan Intl.
ORD
O'Hare Intl.
$204 Roundtrip, found 16 hours ago
$204
Roundtrip
found 16 hours ago
Select Bargain Flight flight, departing Fri, Oct 16 from Logan Intl. to O'Hare Intl., returning Mon, Oct 19, priced at $204 found 16 hours ago
Delta
Tue, Oct 13 - Tue, Oct 20
BOS
Logan Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 16 hours ago
$217
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, Oct 13 from Logan Intl. to O'Hare Intl., returning Tue, Oct 20, priced at $217 found 16 hours ago
American Airlines
Wed, Oct 21 - Sat, Oct 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 18 hours ago
$217
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Wed, Oct 21 from Logan Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $217 found 18 hours ago
JetBlue Airways
Mon, Oct 19 - Sat, Oct 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$226 Roundtrip, found 5 days ago
$226
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Oct 19 from Logan Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $226 found 5 days ago
Frontier Airlines
Sat, Sep 5 - Wed, Sep 9
LAX
Los Angeles Intl.
MDW
Midway Intl.
$230 Roundtrip, found 8 hours ago
$230
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Los Angeles Intl. to Midway Intl., returning Wed, Sep 9, priced at $230 found 8 hours ago
American Airlines
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$250 Roundtrip, just found
$250
Roundtrip
just found
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Tue, Sep 8, priced at $250 just found
Bargain Flight
Wed, Nov 4 - Thu, Nov 5
SEA
Seattle - Tacoma Intl.
ORD
O'Hare Intl.
$255 Roundtrip, found 1 day ago
$255
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Nov 4 from Seattle - Tacoma Intl. to O'Hare Intl., returning Thu, Nov 5, priced at $255 found 1 day ago
American Airlines
Mon, Sep 14 - Thu, Sep 17
IAH
George Bush Intercontinental
RFD
Greater Rockford
$288 Roundtrip, found 16 hours ago
$288
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Mon, Sep 14 from George Bush Intercontinental to Greater Rockford, returning Thu, Sep 17, priced at $288 found 16 hours ago
Frontier Airlines
Thu, Oct 22 - Sun, Oct 25
BOS
Logan Intl.
MDW
Midway Intl.
$325 Roundtrip, found 18 hours ago
$325
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Logan Intl. to Midway Intl., returning Sun, Oct 25, priced at $325 found 18 hours ago
Alaska Airlines
Wed, Nov 4 - Thu, Nov 5
PAE
Seattle Paine Field Intl. Airport
ORD
O'Hare Intl.
$380 Roundtrip, found 1 day ago
$380
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Nov 4 from Seattle Paine Field Intl. Airport to O'Hare Intl., returning Thu, Nov 5, priced at $380 found 1 day ago
American Airlines
Thu, Aug 20 - Mon, Aug 24
SEA
Seattle - Tacoma Intl.
RFD
Greater Rockford
$422 Roundtrip, found 6 days ago
$422
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Aug 20 from Seattle - Tacoma Intl. to Greater Rockford, returning Mon, Aug 24, priced at $422 found 6 days ago
Delta
Thu, Aug 20 - Mon, Aug 24
SEA
Seattle - Tacoma Intl.
MDW
Midway Intl.
$656 Roundtrip, found 6 days ago
$656
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Aug 20 from Seattle - Tacoma Intl. to Midway Intl., returning Mon, Aug 24, priced at $656 found 6 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 October, 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 $108, 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 $108 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$118

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 ...
Get rates
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (1,900 reviews)
"Awesome"

Reviewed on Aug 3, 2026

Get rates
The Chicago Hotel Collection Ambassador Gold Coast
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 ...
Get rates
Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,940 reviews)
"Free airport shuttle and modernized room 10/10"

Reviewed on Aug 3, 2026

Get rates
Hyatt Regency O'Hare Chicago
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
Get rates
The Allegro Royal Sonesta Hotel Chicago Loop
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,232 reviews)
"Great all around"

Reviewed on Aug 3, 2026

Get rates
Hyatt Regency McCormick Place Chicago
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
Get rates
Omni Chicago Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Get rates
The Chicago Hotel Collection - Magnificent Mile
See all 4,978 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)
"This was the worst hotel I’ve ever been to. I paid over $200 a night and the hotel was in terrible condition. My room smelled awful. The staff was not helpful. The whole place smelled like cannabis. The door on my room would barely latch. I attempted to find a different hotel because I did not want ..."

Reviewed on Aug 2, 2026

Get rates
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 ...
Get rates
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 4,978 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.