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Hillside

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Hillside Flights as Low as $66

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

Frontier Airlines
Tue, Aug 4 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$66 Roundtrip, found 10 hours ago
$66
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $66 found 10 hours ago
Frontier Airlines
Tue, Jun 9 - Wed, Jun 17
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$76 Roundtrip, found 15 hours ago
$76
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Jun 17, priced at $76 found 15 hours ago
Bargain Flight
Sun, Jun 14 - Thu, Jun 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 7 hours ago
$177
Roundtrip
found 7 hours ago
Select Bargain Flight flight, departing Sun, Jun 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Jun 18, priced at $177 found 7 hours ago
Bargain Flight
Tue, Nov 3 - Tue, Nov 10
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Nov 3 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Tue, Nov 10, priced at $177 found 1 day ago
American Airlines
Tue, Aug 4 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 10 hours ago
$197
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $197 found 10 hours ago
Delta
Tue, Aug 4 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 10 hours ago
$197
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $197 found 10 hours ago
Frontier Airlines
Tue, Jul 14 - Wed, Jul 15
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$210 Roundtrip, found 19 hours ago
$210
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Tue, Jul 14 from Sky Harbor Intl. to O'Hare Intl., returning Wed, Jul 15, priced at $210 found 19 hours ago
Frontier Airlines
Mon, Aug 10 - Wed, Aug 19
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$230 Roundtrip, found 3 days ago
$230
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Aug 10 from Sky Harbor Intl. to Midway Intl., returning Wed, Aug 19, priced at $230 found 3 days ago
Delta
Wed, Jun 17 - Fri, Jun 26
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$235 Roundtrip, found 11 hours ago
$235
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Jun 17 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Fri, Jun 26, priced at $235 found 11 hours ago
Alaska Airlines
Sun, May 24 - Wed, May 27
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$273 Roundtrip, found 3 days ago
$273
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sun, May 24 from Sky Harbor Intl. to O'Hare Intl., returning Wed, May 27, priced at $273 found 3 days ago
JetBlue Airways
Tue, Aug 4 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$287 Roundtrip, found 10 hours ago
$287
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $287 found 10 hours ago
American Airlines
Thu, Jun 4 - Mon, Jun 8
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jun 4 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Mon, Jun 8, priced at $317 found 1 day ago
American Airlines
Tue, May 26 - Tue, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
RFD
Greater Rockford
$322 Roundtrip, found 4 days ago
$322
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, May 26 from Baltimore Washington Intl. Thurgood Marshall to Greater Rockford, returning Tue, Jun 2, priced at $322 found 4 days ago
American Airlines
Fri, Jun 5 - Mon, Jun 8
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$324 Roundtrip, found 4 days ago
$324
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Jun 5 from Sky Harbor Intl. to Greater Rockford, returning Mon, Jun 8, priced at $324 found 4 days ago
Delta
Tue, Jul 14 - Tue, Jul 28
BHM
Birmingham Intl.
ORD
O'Hare Intl.
$367 Roundtrip, found 3 days ago
$367
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jul 14 from Birmingham Intl. to O'Hare Intl., returning Tue, Jul 28, priced at $367 found 3 days ago
American Airlines
Thu, Jul 2 - Sat, Jul 4
BHM
Birmingham Intl.
RFD
Greater Rockford
$406 Roundtrip, found 12 hours ago
$406
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Thu, Jul 2 from Birmingham Intl. to Greater Rockford, returning Sat, Jul 4, priced at $406 found 12 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 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 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 $66, 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 $66 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$56

Last Minute Hotel Deals in Hillside

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (2,697 reviews)
great location

Reviewed on May 9, 2026

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Hotel Felix River North/Magnificent Mile
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! (10,196 reviews)
Old and historic property. With that being said, not all of the property is renewed but the rooms are kept clean :) service is good and is close to a lot of things in downtown chicago

Reviewed on May 10, 2026

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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 ...
8.8/10 Excellent! (5,192 reviews)
I can only review the staff at The River Hotel is AMAZING to say the least. From the moment I walked through the door I felt at home. I received a warm welcome and a fabulous room with all of the amenities. My room (suite) was spacious, clean and so comfortable. The hotel is centrally located so ...

Reviewed on May 9, 2026

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River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,100 reviews)
Good breakfast, limited hours. Rooms are clean and new

Reviewed on May 10, 2026

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Hotel Riu Plaza Chicago
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 hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,939 reviews)
Yes

Reviewed on May 5, 2026

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Embassy Suites by Hilton Chicago Downtown River North
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (3,503 reviews)
Basic stay not worth paying top dollar for

Reviewed on May 9, 2026

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Club Quarters Hotel, Central Loop, Chicago
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! (4,285 reviews)
Lovely place to stay. Very clean and staff was so polite and helpful!!

Reviewed on May 9, 2026

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Hilton Chicago/Magnificent Mile Suites
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (2,302 reviews)
Beautiful on the surface. Terrible smell of heavy perfume in the rooms. What on earth happened here to require such a strong smell to cover it up? All the hotel provided soaps and lotions are heavy scented dollar store brands. Pack your own. No maid service until late in the day, after 3:30pm. We ...

Reviewed on May 9, 2026

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Holiday Inn Chicago Dwtn - The Mart by IHG
See all 5,158 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! (1,007 reviews)
Excellent facilities, ideal and safe parking.

Reviewed on May 6, 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 ...
7/10 Good! (1,003 reviews)
The beds were NOT comfortable.

Reviewed on May 7, 2026

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Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 5,158 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.