Search Cheap Flights to
Hillside

Name: Hyatt Regency Chicago
Rating: 9.4

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Hillside Flights as Low as $70

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

All deals

One way

Roundtrip

Sat, Apr 25 - Sat, May 2

ATL

Hartsfield-Jackson Atlanta Intl.

MDW

Midway Intl.

$70

Roundtrip

found 21 hours ago

Sat, May 2 - Tue, May 5

ATL

Hartsfield-Jackson Atlanta Intl.

ORD

O'Hare Intl.

$76

Roundtrip

found 13 hours ago

Wed, Apr 29 - Sat, May 2

ATL

Hartsfield-Jackson Atlanta Intl.

ORD

O'Hare Intl.

$85

Roundtrip

found 13 hours ago

Thu, May 28 - Sat, Jun 6

LAX

Los Angeles Intl.

ORD

O'Hare Intl.

$110

Roundtrip

found 23 hours ago

Mon, May 4 - Mon, May 11

AUS

Austin-Bergstrom Intl.

ORD

O'Hare Intl.

$136

Roundtrip

found 3 days ago

Thu, Apr 30 - Sat, May 2

IAD

Washington Dulles Intl.

ORD

O'Hare Intl.

$170

Roundtrip

found 3 days ago

Fri, Apr 17 - Sun, Apr 19

ATL

Hartsfield-Jackson Atlanta Intl.

ORD

O'Hare Intl.

$173

Roundtrip

found 13 hours ago

Tue, May 5 - Sat, May 9

LAX

Los Angeles Intl.

MDW

Midway Intl.

$175

Roundtrip

found 1 day ago

Tue, May 5 - Tue, May 12

IAD

Washington Dulles Intl.

MDW

Midway Intl.

$180

Roundtrip

found 2 days ago

Mon, Jun 8 - Wed, Jun 10

AUS

Austin-Bergstrom Intl.

MDW

Midway Intl.

$185

Roundtrip

found 2 days ago

Wed, May 13 - Wed, May 13

ATL

Hartsfield-Jackson Atlanta Intl.

MDW

Midway Intl.

$195

Roundtrip

found 2 days ago

Wed, May 13 - Wed, May 13

ATL

Hartsfield-Jackson Atlanta Intl.

ORD

O'Hare Intl.

$202

Roundtrip

found 11 hours ago

Thu, May 14 - Mon, May 18

ATL

Hartsfield-Jackson Atlanta Intl.

RFD

Greater Rockford

$315

Roundtrip

found 17 hours ago

Mon, May 25 - Tue, May 26

LAX

Los Angeles Intl.

RFD

Greater Rockford

$316

Roundtrip

found 3 days ago

Wed, May 6 - Thu, May 7

LAX

Los Angeles Intl.

ORD

O'Hare Intl.

$337

Roundtrip

found 2 days ago

Fri, Sep 4 - Sat, Sep 5

AUS

Austin-Bergstrom Intl.

RFD

Greater Rockford

$373

Roundtrip

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 April, 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 $70, 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 $70 right now, why wait?

Hillside Flight Information
Destination airport	Midway Intl.
Destination airport IATA code	MDW
Roundtrip price	$70

Last Minute Hotel Deals in Hillside

151 East Wacker Dr Chicago IL

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...

9.4/10 Exceptional! (3,501 reviews)

YES

Reviewed on Apr 14, 2026

Get rates

See all 5,197 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

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! (1,000 reviews)

Room was clean. But towels may have smelled dusty. Everyone was nice. The bartender and restaurant food were excellent. Check in and check out were simple

Reviewed on Apr 7, 2026

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Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

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! (1,003 reviews)

Staff never answer the phone it’s ridiculous because what if there was an emergency or something kids running through the hallways all night very loud and loud music coming from other rooms it was horrible room 212 had bus in there definitely wasn’t worth my time or the amount they ask for per room ...

Reviewed on Apr 4, 2026

Get rates

See all 5,197 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.

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