Search Cheap Flights to
Hillside

Photo by Off The Beaten Track

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Hillside Flights as Low as $72

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

Spirit Airlines
Wed, Aug 27 - Wed, Sep 3
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 22 hours ago
$72
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Wed, Aug 27 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Sep 3, priced at $72 found 22 hours ago
Frontier Airlines
Wed, Aug 27 - Wed, Sep 3
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$99 Roundtrip, found 22 hours ago
$99
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Wed, Aug 27 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Sep 3, priced at $99 found 22 hours ago
Frontier Airlines
Sat, Aug 30 - Wed, Sep 3
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$105 Roundtrip, found 10 hours ago
$105
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 3, priced at $105 found 10 hours ago
Spirit Airlines
Sat, Sep 27 - Mon, Sep 29
LGA
LaGuardia
ORD
O'Hare Intl.
$106 Roundtrip, found 6 days ago
$106
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sat, Sep 27 from LaGuardia to O'Hare Intl., returning Mon, Sep 29, priced at $106 found 6 days ago
Frontier Airlines
Thu, Sep 11 - Sun, Sep 14
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 13 hours ago
$117
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Charlotte-Douglas Intl. to O'Hare Intl., returning Sun, Sep 14, priced at $117 found 13 hours ago
Delta
Sun, Aug 31 - Wed, Sep 3
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$119 Roundtrip, found 10 hours ago
$119
Roundtrip
found 10 hours ago
Select Delta flight, departing Sun, Aug 31 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 3, priced at $119 found 10 hours ago
Spirit Airlines
Fri, Oct 17 - Mon, Oct 20
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Fri, Oct 17 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Oct 20, priced at $120 found 2 days ago
United
Thu, Sep 11 - Mon, Sep 15
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$129 Roundtrip, found 17 hours ago
$129
Roundtrip
found 17 hours ago
Select United flight, departing Thu, Sep 11 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Sep 15, priced at $129 found 17 hours ago
American Airlines
Thu, Sep 11 - Mon, Sep 15
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$129 Roundtrip, found 17 hours ago
$129
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Thu, Sep 11 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Sep 15, priced at $129 found 17 hours ago
Frontier Airlines
Mon, Aug 25 - Wed, Sep 3
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$160 Roundtrip, found 21 hours ago
$160
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Mon, Aug 25 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Sep 3, priced at $160 found 21 hours ago
Delta
Tue, Sep 9 - Tue, Sep 9
DAL
Love Field
ORD
O'Hare Intl.
$194 Roundtrip, found 3 days ago
$194
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 9, priced at $194 found 3 days ago
Frontier Airlines
Sat, Aug 30 - Sun, Aug 31
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Charlotte-Douglas Intl. to Midway Intl., returning Sun, Aug 31, priced at $196 found 1 day ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 1 day ago
Contour Airlines
Mon, Sep 8 - Thu, Sep 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$203 Roundtrip, found 3 days ago
$203
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Mon, Sep 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $203 found 3 days ago
Frontier Airlines
Wed, Sep 3 - Sat, Sep 6
LGA
LaGuardia
MDW
Midway Intl.
$212 Roundtrip, found 6 days ago
$212
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Sep 3 from LaGuardia to Midway Intl., returning Sat, Sep 6, priced at $212 found 6 days ago
JetBlue Airways
Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$283 Roundtrip, found 1 day ago
$283
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Oct 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 22, priced at $283 found 1 day 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 August, 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 $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
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$90

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 free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,950 reviews)
"The room and bathroom were both spacious with high ceilings. Great view on the lake side."

Reviewed on Aug 3, 2025

Get rates
Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,824 reviews)
"could not use my Plat Amex, to upgrade bc of expedia."

Reviewed on Aug 3, 2025

Get rates
Palmer House a Hilton 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! (1,333 reviews)
"Nice location"

Reviewed on Aug 1, 2025

Get rates
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
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. ...
8.4/10 Very Good! (3,628 reviews)
"."

Reviewed on Aug 1, 2025

Get rates
Hilton Garden Inn Chicago Downtown/Magnificent Mile
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. ...
8.4/10 Very Good! (4,618 reviews)
Amazing hotel stay!
"The hotel was beautiful & spacious. All of the staff were courteous & friendly. They offer 2 free complimentary drinks a day during happy hour & the complimentary breakfast has plenty of options; pancakes, eggs, sausage, hash browns, toast/bagel/muffin station, oatmeal station, cereal bar & a build ..."

Reviewed on Aug 4, 2025

Get rates
Embassy Suites by Hilton Chicago Downtown River North
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! (3,501 reviews)
"The rooms are small but everything else was amazing I upgraded to a wheelchair room"

Reviewed on Aug 2, 2025

Get rates
citizenM Chicago Downtown
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! (2,564 reviews)
"Nice clean hotel, good location."

Reviewed on Aug 2, 2025

Get rates
Hilton Chicago/Magnificent Mile Suites
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,161 reviews)
"Great view"

Reviewed on Aug 2, 2025

Get rates
InterContinental Chicago Magnificent Mile by IHG
See all 5,191 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
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! (1,003 reviews)
"Hotel needs major upgrades."

Reviewed on Jul 19, 2025

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 ...
6.8/10 (1,003 reviews)
"The room and included breakfast were great. However, the two elevators had issues the entire stay with very little communication about when or if those issues would be fixed. We were on the 4th floor, so it mattered."

Reviewed on Jul 30, 2025

Get rates
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 5,191 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.