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Hillside

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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, Nov 5 - Fri, Nov 6
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Nov 5 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Fri, Nov 6, priced at $68 found 6 days ago
Frontier Airlines
Tue, Oct 6 - Wed, Oct 21
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 10 hours ago
$83
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Tue, Oct 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 21, priced at $83 found 10 hours ago
Frontier Airlines
Tue, Nov 17 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 1 day ago
$84
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Nov 19, priced at $84 found 1 day ago
Frontier Airlines
Tue, Nov 10 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$86 Roundtrip, found 8 hours ago
$86
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Nov 10 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Nov 19, priced at $86 found 8 hours ago
Frontier Airlines
Wed, Dec 2 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$104 Roundtrip, found 8 hours ago
$104
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 15, priced at $104 found 8 hours ago
Bargain Flight
Thu, Nov 26 - Thu, Dec 17
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$176 Roundtrip, found 15 hours ago
$176
Roundtrip
found 15 hours ago
Select Bargain Flight flight, departing Thu, Nov 26 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Dec 17, priced at $176 found 15 hours ago
Southwest Airlines
Wed, Dec 2 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$199 Roundtrip, found 8 hours ago
$199
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 15, priced at $199 found 8 hours ago
Bargain Flight
Mon, Nov 16 - Wed, Nov 18
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$204 Roundtrip, found 20 hours ago
$204
Roundtrip
found 20 hours ago
Select Bargain Flight flight, departing Mon, Nov 16 from Ronald Reagan Washington National to O'Hare Intl., returning Wed, Nov 18, priced at $204 found 20 hours ago
Frontier Airlines
Tue, Sep 22 - Sat, Oct 10
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$227 Roundtrip, found 5 days ago
$227
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Sat, Oct 10, priced at $227 found 5 days ago
Frontier Airlines
Wed, Oct 28 - Sat, Oct 31
IAD
Washington Dulles Intl.
MDW
Midway Intl.
$234 Roundtrip, found 7 hours ago
$234
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Oct 28 from Washington Dulles Intl. to Midway Intl., returning Sat, Oct 31, priced at $234 found 7 hours ago
Frontier Airlines
Wed, Oct 28 - Sat, Oct 31
IAD
Washington Dulles Intl.
ORD
O'Hare Intl.
$234 Roundtrip, found 1 hour ago
$234
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Oct 28 from Washington Dulles Intl. to O'Hare Intl., returning Sat, Oct 31, priced at $234 found 1 hour ago
Southwest Airlines
Fri, Nov 27 - Tue, Dec 1
DCA
Ronald Reagan Washington National
MDW
Midway Intl.
$255 Roundtrip, just found
$255
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Nov 27 from Ronald Reagan Washington National to Midway Intl., returning Tue, Dec 1, priced at $255 just found
Delta
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$287 Roundtrip, found 8 hours ago
$287
Roundtrip
found 8 hours ago
Select Delta flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $287 found 8 hours ago
American Airlines
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$287 Roundtrip, found 8 hours ago
$287
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $287 found 8 hours ago
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$383 Roundtrip, found 8 hours ago
$383
Roundtrip
found 8 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 $383 found 8 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Sep 21 - Sat, Sep 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$507 Roundtrip, found 1 hour ago
$507
Roundtrip
found 1 hour ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Sep 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 26, priced at $507 found 1 hour 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 November, 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 14 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

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 ...
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The Chicago Hotel Collection Ambassador Gold Coast
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! (10,243 reviews)
"The hotel overall was nice and the room is clean. The dining room at the hotel was very slow, and the food was terrible except for that. The experience was good."

Reviewed on Sep 14, 2026

Get rates
Congress Plaza Hotel
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! (3,209 reviews)
"Great stay!"

Reviewed on Sep 14, 2026

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Hilton 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! (2,165 reviews)
"Great!"

Reviewed on Sep 13, 2026

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The Chicago Hotel Collection - Magnificent Mile
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
8/10 Very Good! (1,612 reviews)
"The service was great and hotel was cleaned. We will definitely stay here again"

Reviewed on Sep 14, 2026

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Hampton Inn Chicago Downtown/Magnificent Mile
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
9.6/10 Exceptional! (4,799 reviews)
"They don’t have swimming pool which was a little bit sad but they parked my car for me and brought it back when I was leaving"

Reviewed on Sep 14, 2026

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L7 Chicago by LOTTE
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
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Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
See all 4,989 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! (1,009 reviews)
"Breakfast was delicious"

Reviewed on Sep 13, 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 ...
Get rates
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 4,989 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.