Search Cheap Flights to
Hillside

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Hillside Flights as Low as $58

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

Frontier Airlines
Wed, Feb 26 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 3 days ago
$58
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Feb 26 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Mar 4, priced at $58 found 3 days ago
Frontier Airlines
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 2 hours ago
$63
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $63 found 2 hours ago
Frontier Airlines
Tue, Feb 18 - Tue, Feb 25
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$63 Roundtrip, found 4 days ago
$63
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Feb 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Feb 25, priced at $63 found 4 days ago
Frontier Airlines
Wed, Jan 22 - Tue, Jan 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 3 hours ago
$68
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Jan 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jan 28, priced at $68 found 3 hours ago
Frontier Airlines
Tue, Mar 4 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 7 hours ago
$73
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Mar 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 4, priced at $73 found 7 hours ago
Spirit Airlines
Wed, Jan 22 - Tue, Jan 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$113 Roundtrip, found 3 hours ago
$113
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Wed, Jan 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jan 28, priced at $113 found 3 hours ago
Frontier Airlines
Thu, Jan 9 - Mon, Jan 13
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$118 Roundtrip, found 8 hours ago
$118
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Jan 9 from George Bush Intercontinental to O'Hare Intl., returning Mon, Jan 13, priced at $118 found 8 hours ago
Spirit Airlines
Wed, Jan 29 - Thu, Jan 30
BOS
Logan Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jan 29 from Logan Intl. to O'Hare Intl., returning Thu, Jan 30, priced at $119 found 2 days ago
Delta
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 2 hours ago
$132
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $132 found 2 hours ago
American Airlines
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 2 hours ago
$132
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $132 found 2 hours ago
United
Wed, Feb 12 - Sat, Feb 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 1 hour ago
$137
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Feb 12 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Feb 15, priced at $137 found 1 hour ago
JetBlue Airways
Wed, Jan 29 - Thu, Jan 30
BOS
Logan Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Jan 29 from Logan Intl. to O'Hare Intl., returning Thu, Jan 30, priced at $157 found 2 days ago
Frontier Airlines
Fri, Jan 10 - Sun, Jan 12
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jan 10 from Ronald Reagan Washington National to O'Hare Intl., returning Sun, Jan 12, priced at $165 found 1 day ago
Frontier Airlines
Tue, Dec 31 - Tue, Jan 7
BOS
Logan Intl.
MDW
Midway Intl.
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Dec 31 from Logan Intl. to Midway Intl., returning Tue, Jan 7, priced at $188 found 2 days ago
Frontier Airlines
Fri, Jan 10 - Sun, Jan 12
DCA
Ronald Reagan Washington National
MDW
Midway Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jan 10 from Ronald Reagan Washington National to Midway Intl., returning Sun, Jan 12, priced at $199 found 1 day ago
Frontier Airlines
Wed, Dec 25 - Tue, Dec 31
IAH
George Bush Intercontinental
MDW
Midway Intl.
$438 Roundtrip, found 3 days ago
$438
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Dec 25 from George Bush Intercontinental to Midway Intl., returning Tue, Dec 31, priced at $438 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 February, 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 $58, 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 $58 right now, why wait?

Hillside Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$58

Last Minute Hotel Deals in Hillside

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $143 per night from Dec 24 to Dec 25
$143
includes taxes & fees
Dec 24 - Dec 25
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,287 reviews)
The Congress hotel is the best
"I love staying at the Congress hotel whenever I’m in Chicago"

Reviewed on Dec 22, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $109 per night from Jan 22 to Jan 23
$109
includes taxes & fees
Jan 22 - Jan 23, 2025
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,626 reviews)
"Having to park my car 4 blocks away"

Reviewed on Dec 22, 2024

River Hotel
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
The price is $193 per night from Jan 10 to Jan 11
$193
includes taxes & fees
Jan 10 - Jan 11, 2025
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
9/10 Wonderful! (3,118 reviews)
"Esta muy bien ubicado,cerca de casi todos los puntos turisticos,muy tranquilo ,limpio ,el unico detalle q le note el agua de la ducha no tiene fuerza ,pero no es nada como para no volver ,es solo un detalle.por el resto regresaria mil veces."

Reviewed on Dec 20, 2024

Hyatt Regency Chicago
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
The price is $133 per night from Jan 7 to Jan 8
$133
includes taxes & fees
Jan 7 - Jan 8, 2025
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,288 reviews)
"I loved the pool, it was very big and spaceous and the water temp was perfect. The room it self was also nice. would def recommend coming back."

Reviewed on Dec 22, 2024

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $113 per night from Jan 5 to Jan 6
$113
includes taxes & fees
Jan 5 - Jan 6, 2025
Stay at this 4-star 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 ...
8.6/10 Excellent! (2,782 reviews)
"Staff was attentive and friendly. Highly recommend."

Reviewed on Dec 18, 2024

Eurostars Magnificent Mile
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
The price is $169 per night from Dec 29 to Dec 30
$169
includes taxes & fees
Dec 29 - Dec 30
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,502 reviews)
"The room was comfortable and I enjoyed seeing the hotel beautifully decorated for Christmas. All staff members were polite and very helpful. Thank you for the experience."

Reviewed on Dec 20, 2024

Hilton Chicago
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is $131 per night from Dec 24 to Dec 25
$131
includes taxes & fees
Dec 24 - Dec 25
Stay at this 4-star family-friendly hotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and in-room massages. Our guests praise the ...
8/10 Very Good! (2,797 reviews)
"Great location on Michigan Ave. Nice walk to area attractions, shopping and restaurants. Could use a little updating. Bed was not the best."

Reviewed on Dec 18, 2024

Warwick Allerton - Chicago
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
The price is $118 per night from Jan 13 to Jan 14
$118
includes taxes & fees
Jan 13 - Jan 14, 2025
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
7.8/10 Good! (1,370 reviews)
Staycation at it’s Finest!
"Our stay was a short one, but enjoyed our stay in it’s entirely. Staff was more than welcoming, providing complementary upgrade options and added time to our check-out. There was a bar and nice and cozy reception area! We would definitely recommend!"

Reviewed on Dec 21, 2024

Hotel Felix River North/Magnificent Mile
See all 4,602 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
The price is $98 per night from Dec 29 to Dec 30
$98
includes taxes & fees
Dec 29 - Dec 30
Stay at this 3-star business-friendly hotel in Hillside. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
7.4/10 Good! (999 reviews)
"Ok"

Reviewed on Dec 16, 2024

Best Western Plus Chicago Hillside
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area
2.5 out of 5
200 S Mannheim Road, Hillside, IL
The price is $105 per night from Dec 29 to Dec 30
$105
includes taxes & fees
Dec 29 - Dec 30
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 ...
6.8/10 (1,005 reviews)
"There were plenty of options to dine. The stores were within walking distance."

Reviewed on Dec 22, 2024

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area
See all 4,602 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.