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Hillside

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Hillside Flights as Low as $100

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

Frontier Airlines
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 4 hours ago
$100
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $100 found 4 hours ago
Frontier Airlines
Tue, Nov 17 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$156 Roundtrip, found 7 hours ago
$156
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Thu, Nov 19, priced at $156 found 7 hours ago
Southwest Airlines
Wed, Dec 2 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$166 Roundtrip, found 12 hours ago
$166
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 15, priced at $166 found 12 hours ago
Bargain Flight
Sat, Oct 24 - Thu, Oct 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$168 Roundtrip, found 8 hours ago
$168
Roundtrip
found 8 hours ago
Select Bargain Flight flight, departing Sat, Oct 24 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Oct 29, priced at $168 found 8 hours ago
American Airlines
Wed, Nov 11 - Wed, Nov 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$194 Roundtrip, found 2 hours ago
$194
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Nov 11 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $194 found 2 hours ago
Delta
Wed, Nov 11 - Wed, Nov 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$194 Roundtrip, found 2 hours ago
$194
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Nov 11 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $194 found 2 hours ago
United
Fri, Nov 13 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 5 hours ago
$197
Roundtrip
found 5 hours ago
Select United flight, departing Fri, Nov 13 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $197 found 5 hours ago
Southwest Airlines
Mon, Nov 9 - Fri, Nov 13
LAX
Los Angeles Intl.
MDW
Midway Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Nov 9 from Los Angeles Intl. to Midway Intl., returning Fri, Nov 13, priced at $200 found 1 day ago
Southwest Airlines
Tue, Nov 10 - Sat, Nov 14
BOS
Logan Intl.
MDW
Midway Intl.
$205 Roundtrip, found 13 hours ago
$205
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Tue, Nov 10 from Logan Intl. to Midway Intl., returning Sat, Nov 14, priced at $205 found 13 hours ago
Bargain Flight
Tue, Nov 10 - Tue, Nov 17
BOS
Logan Intl.
ORD
O'Hare Intl.
$208 Roundtrip, found 5 days ago
$208
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Tue, Nov 10 from Logan Intl. to O'Hare Intl., returning Tue, Nov 17, priced at $208 found 5 days ago
Frontier Airlines
Mon, Dec 21 - Mon, Jan 11
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Dec 21 from Sky Harbor Intl. to O'Hare Intl., returning Mon, Jan 11, priced at $224 found 1 day ago
Bargain Flight
Mon, Oct 26 - Thu, Oct 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$240 Roundtrip, found 7 hours ago
$240
Roundtrip
found 7 hours ago
Select Bargain Flight flight, departing Mon, Oct 26 from Los Angeles Intl. to O'Hare Intl., returning Thu, Oct 29, priced at $240 found 7 hours ago
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$295 Roundtrip, found 4 hours ago
$295
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $295 found 4 hours ago
Southwest Airlines
Fri, Dec 18 - Tue, Dec 22
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$319 Roundtrip, found 17 hours ago
$319
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Fri, Dec 18 from Sky Harbor Intl. to Midway Intl., returning Tue, Dec 22, priced at $319 found 17 hours ago
Sun Country Airlines
Fri, Dec 18 - Tue, Dec 22
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$448 Roundtrip, found 17 hours ago
$448
Roundtrip
found 17 hours ago
Select Sun Country Airlines flight, departing Fri, Dec 18 from Sky Harbor Intl. to O'Hare Intl., returning Tue, Dec 22, priced at $448 found 17 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Sun, Dec 20 - Sat, Dec 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$459 Roundtrip, found 4 days ago
$459
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Dec 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 26, priced at $459 found 4 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 December, 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 13 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 $100, 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 $100 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$99

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 ...
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Congress Plaza Hotel
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 ...
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River 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! (2,417 reviews)
"The staff was just blatantly unhelpful. The front desk was often unmanned and could not take requests whether it was for a checkout or to ask about how a food delivery had been misplaced. I’ve seen HolidayInns with better customer service."

Reviewed on Oct 5, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
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 ...
8/10 Very Good! (2,318 reviews)
"N:a"

Reviewed on Oct 5, 2026

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The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,363 reviews)
"Solid 4 out of 5 star hotel. Great location and helpful staff. No room service keeps it from 5 star territory."

Reviewed on Oct 5, 2026

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Hilton Chicago
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
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Eurostars Magnificent Mile
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
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! (3,489 reviews)
"The room was spacious and the bed was very comfortable. The check in was easy and they gave us a voucher for a drink in the lounge bar. We had a very nice stay. Great location, the river walk is with in walking distance."

Reviewed on Oct 4, 2026

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Hyatt Regency Chicago
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (2,122 reviews)
"Everything was super clean They made the bed everyday and made sure we had fresh towels. Every time we went into the elevator the staff was very friendly and even asked how our day was going or did we slept well"

Reviewed on Oct 5, 2026

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The Wade
See all 5,050 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)
"Bien todo sin problemas cerca solo la dirección fue confusa"

Reviewed on Oct 4, 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 ...
Get rates
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 5,050 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.