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 $68

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

Frontier Airlines
Thu, May 28 - Wed, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 3 days ago
$68
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, May 28 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $68 found 3 days ago
Frontier Airlines
Tue, Sep 15 - Tue, Sep 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$71 Roundtrip, found 2 days ago
$71
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Sep 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 15, priced at $71 found 2 days ago
Frontier Airlines
Wed, Sep 9 - Tue, Sep 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$77 Roundtrip, found 15 hours ago
$77
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Wed, Sep 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 22, priced at $77 found 15 hours ago
Frontier Airlines
Wed, May 27 - Tue, Jun 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$78 Roundtrip, found 4 days ago
$78
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, May 27 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jun 9, priced at $78 found 4 days ago
Delta
Wed, Jul 1 - Wed, Jul 22
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jul 1 from Minneapolis - St. Paul Intl. to Midway Intl., returning Wed, Jul 22, priced at $117 found 2 days ago
American Airlines
Wed, Jul 29 - Tue, Aug 18
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jul 29 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, Aug 18, priced at $137 found 1 day ago
United
Wed, Jul 29 - Tue, Aug 18
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jul 29 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, Aug 18, priced at $137 found 1 day ago
Frontier Airlines
Sat, Jul 4 - Wed, Jul 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$158 Roundtrip, found 14 hours ago
$158
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, Jul 4 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 8, priced at $158 found 14 hours ago
Sun Country Airlines
Fri, Sep 18 - Mon, Sep 21
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 5 days ago
$167
Roundtrip
found 5 days ago
Select Sun Country Airlines flight, departing Fri, Sep 18 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Sep 21, priced at $167 found 5 days ago
Bargain Flight
Sat, Jun 6 - Tue, Jun 9
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$188 Roundtrip, found 5 days ago
$188
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Sat, Jun 6 from Ronald Reagan Washington National to O'Hare Intl., returning Tue, Jun 9, priced at $188 found 5 days ago
Delta
Tue, Jun 9 - Tue, Jun 16
LAX
Los Angeles Intl.
MDW
Midway Intl.
$224 Roundtrip, found 5 days ago
$224
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jun 9 from Los Angeles Intl. to Midway Intl., returning Tue, Jun 16, priced at $224 found 5 days ago
Delta
Sat, Aug 22 - Sat, Aug 22
DCA
Ronald Reagan Washington National
MDW
Midway Intl.
$259 Roundtrip, found 2 days ago
$259
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Aug 22 from Ronald Reagan Washington National to Midway Intl., returning Sat, Aug 22, priced at $259 found 2 days ago
American Airlines
Sat, Jun 20 - Tue, Jun 23
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$276 Roundtrip, found 13 hours ago
$276
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Jun 20 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Tue, Jun 23, priced at $276 found 13 hours ago
JetBlue Airways
Tue, Aug 4 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$297 Roundtrip, just found
$297
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $297 just found
Alaska Airlines
Fri, May 29 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$314 Roundtrip, found 2 days ago
$314
Roundtrip
found 2 days 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 2 days ago
American Airlines
Sun, May 24 - Sun, May 31
LAX
Los Angeles Intl.
RFD
Greater Rockford
$404 Roundtrip, found 6 days ago
$404
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, May 24 from Los Angeles Intl. to Greater Rockford, returning Sun, May 31, priced at $404 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 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 $68, 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 $68 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$68

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! (10,137 reviews)
The bar was very welcoming and the historic ambience and location was exceptional

Reviewed on May 16, 2026

Get rates
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! (4,160 reviews)
Perfect central location, friendly staff, exceptional views from the rooftop bar. Would definitely recommend!

Reviewed on May 16, 2026

Get rates
Hotel Riu Plaza Chicago
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 ...
7.8/10 Good! (1,417 reviews)
Everything was nice, the only thing is that there should be a little bid more personel in the lobby taking care of guess needs

Reviewed on May 15, 2026

Get rates
The Chicago Hotel Collection - Magnificent Mile
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! (2,698 reviews)
It was very close to restuarants, easy to find and very accessible. All staff were really helpful.

Reviewed on May 16, 2026

Get rates
Hotel Felix River North/Magnificent Mile
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! (5,183 reviews)
Good for business not really a vacation spot for me. No breakfast and small personal room

Reviewed on May 16, 2026

Get rates
River Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (2,999 reviews)
I enjoyed my stay. The room was clean and the staff were pleasant. I accessed the hotel easily using public transportation. I had a great experience at the cafe for breakfast during a previous stay.

Reviewed on May 16, 2026

Get rates
Freehand Chicago
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! (2,315 reviews)
Very close to everything

Reviewed on May 16, 2026

Get rates
Holiday Inn Chicago Dwtn - The Mart by IHG
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 luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Get rates
Fairmont Chicago at Millennium Park
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! (1,001 reviews)
Clean room nice stat

Reviewed on May 11, 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 ...
7/10 Good! (1,004 reviews)
Room was good. Just noisy from street.

Reviewed on May 15, 2026

Get rates
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.