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Hillside

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Hillside Flights as Low as $84

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

Frontier Airlines
Tue, Jul 28 - Tue, Aug 11
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 5 days ago
$84
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Jul 28 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $84 found 5 days ago
Frontier Airlines
Wed, Jul 1 - Sat, Jul 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$115 Roundtrip, found 18 hours ago
$115
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Wed, Jul 1 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Jul 4, priced at $115 found 18 hours ago
Frontier Airlines
Wed, Aug 19 - Thu, Aug 20
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 4 days ago
$118
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 20, priced at $118 found 4 days ago
Frontier Airlines
Wed, Sep 30 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$138 Roundtrip, found 12 hours ago
$138
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Wed, Sep 30 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 30, priced at $138 found 12 hours ago
United
Wed, Jul 8 - Tue, Jul 14
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Select United flight, departing Wed, Jul 8 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Tue, Jul 14, priced at $171 found 5 days ago
JetBlue Airways
Tue, Aug 25 - Sat, Sep 12
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 21 hours ago
$171
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Tue, Aug 25 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Sat, Sep 12, priced at $171 found 21 hours ago
American Airlines
Wed, Aug 19 - Wed, Aug 26
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Aug 19 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Wed, Aug 26, priced at $171 found 5 days ago
Frontier Airlines
Tue, Jul 14 - Tue, Jul 21
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$187 Roundtrip, found 13 hours ago
$187
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Jul 14 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Jul 21, priced at $187 found 13 hours ago
Delta
Wed, Sep 30 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$192 Roundtrip, found 12 hours ago
$192
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, Sep 30 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 30, priced at $192 found 12 hours ago
American Airlines
Fri, Jul 24 - Fri, Jul 31
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$256 Roundtrip, found 12 hours ago
$256
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Fri, Jul 24 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, Jul 31, priced at $256 found 12 hours ago
Frontier Airlines
Wed, Jun 24 - Thu, Jul 2
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$267 Roundtrip, found 4 days ago
$267
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Jun 24 from Fort Lauderdale - Hollywood Intl. to Midway Intl., returning Thu, Jul 2, priced at $267 found 4 days ago
Contour Airlines
Sat, Aug 29 - Mon, Aug 31
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$289 Roundtrip, just found
$289
Roundtrip
just found
Select Contour Airlines flight, departing Sat, Aug 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Aug 31, priced at $289 just found
Delta
Sat, Aug 29 - Tue, Sep 15
DAL
Love Field
MDW
Midway Intl.
$291 Roundtrip, found 1 day ago
$291
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 29 from Love Field to Midway Intl., returning Tue, Sep 15, priced at $291 found 1 day ago
Delta
Sat, Aug 29 - Tue, Sep 1
DAL
Love Field
ORD
O'Hare Intl.
$291 Roundtrip, found 1 day ago
$291
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 29 from Love Field to O'Hare Intl., returning Tue, Sep 1, priced at $291 found 1 day ago
Sun Country Airlines
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$372 Roundtrip, found 3 hours ago
$372
Roundtrip
found 3 hours ago
Select Sun Country Airlines flight, departing Thu, Aug 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 23, priced at $372 found 3 hours ago
Alaska Airlines
Thu, May 6 - Mon, May 10
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$730 Roundtrip, found 23 hours ago
$730
Roundtrip
found 23 hours ago
Select Alaska Airlines flight, departing Thu, May 6 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, May 10, priced at $730 found 23 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 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 $84, 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 $84 right now, why wait?

Hillside Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$220

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! (10,169 reviews)
"easy walk to soldier field."

Reviewed on Jun 23, 2026

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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 ...
9/10 Wonderful! (4,466 reviews)
"Had a wonderful stay!"

Reviewed on Jun 23, 2026

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Hilton Chicago/Magnificent Mile Suites
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! (1,618 reviews)
"Stunning room, lobby, and spectacular views from the rooftop lounge. That being said, room service could’ve been more attentive. We asked for body wash for our room, as it was out when we checked in. Even after calling the front desk, this small request went unanswered. Barring that, it was a good ..."

Reviewed on Jun 23, 2026

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The Chicago Hotel Collection - Magnificent Mile
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! (2,722 reviews)
"Easy check process and secured parking. Great cleaning service and overall good area to stay."

Reviewed on Jun 23, 2026

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Hyatt Regency O'Hare Chicago
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 ...
8.2/10 Very Good! (1,636 reviews)
"Requested daily cleaning services. Only one day room was cleaned."

Reviewed on Jun 23, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
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! (5,263 reviews)
"Had a wonderful time on a guys trip. Hotel was perfect location and staff were very accommodating."

Reviewed on Jun 23, 2026

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River Hotel
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7.6/10 Good! (2,643 reviews)
"Bathroom was extremely small. Pipes extruded from the walls. Electrical outlets attached to desk didn’t work. Had to unplug TV outlet to use coffee maker. Room used a window unit for a/c. Bed was very comfortable. Facility accommodation were outdated. Wouldn’t have chosen if Wyndham hadn’t beef attached ..."

Reviewed on Jun 23, 2026

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Travelodge by Wyndham Downtown Chicago
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 ...
8.4/10 Very Good! (2,323 reviews)
"I love how convenient this hotel is. However they should FIRE their designer. Whoever thought shag carpets work with rolling luggage has never been a guest at the hotel. The room hallways have a lower profile carpet but still difficult. Even the maintenance people joke about it; not really funny ..."

Reviewed on Jun 22, 2026

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Hilton Chicago O'Hare Airport
See all 5,127 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! (1,008 reviews)
"All was good for us during our stay, no complaints about any of the above."

Reviewed on Jun 22, 2026

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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 ...
7.2/10 Good! (1,009 reviews)
"Amazing staff is great love that there are all Dove products !!!!"

Reviewed on Jun 22, 2026

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Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 5,127 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.