Search Cheap Flights to
Hillside

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Hillside Flights as Low as $98

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

Frontier Airlines
Mon, Nov 3 - Thu, Nov 6
DEN
Denver Intl.
MDW
Midway Intl.
$98 Roundtrip, found 14 hours ago
$98
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Denver Intl. to Midway Intl., returning Thu, Nov 6, priced at $98 found 14 hours ago
Frontier Airlines
Thu, Sep 11 - Thu, Sep 18
DEN
Denver Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 19 hours ago
$100
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Denver Intl. to O'Hare Intl., returning Thu, Sep 18, priced at $100 found 19 hours ago
Frontier Airlines
Sun, Nov 2 - Thu, Nov 6
DEN
Denver Intl.
MDW
Midway Intl.
$110 Roundtrip, found 14 hours ago
$110
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sun, Nov 2 from Denver Intl. to Midway Intl., returning Thu, Nov 6, priced at $110 found 14 hours ago
Frontier Airlines
Thu, Sep 11 - Sun, Sep 21
DEN
Denver Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 19 hours ago
$112
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Denver Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $112 found 19 hours ago
Frontier Airlines
Thu, Sep 11 - Mon, Sep 22
DEN
Denver Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 19 hours ago
$120
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Denver Intl. to O'Hare Intl., returning Mon, Sep 22, priced at $120 found 19 hours ago
Frontier Airlines
Wed, Oct 8 - Wed, Oct 15
DEN
Denver Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 6 days ago
$120
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Oct 8 from Denver Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $120 found 6 days ago
Frontier Airlines
Sun, Nov 2 - Fri, Nov 7
DEN
Denver Intl.
MDW
Midway Intl.
$122 Roundtrip, found 14 hours ago
$122
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sun, Nov 2 from Denver Intl. to Midway Intl., returning Fri, Nov 7, priced at $122 found 14 hours ago
Frontier Airlines
Thu, Sep 11 - Sat, Sep 20
DEN
Denver Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 19 hours ago
$124
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Thu, Sep 11 from Denver Intl. to O'Hare Intl., returning Sat, Sep 20, priced at $124 found 19 hours ago
Frontier Airlines
Fri, Sep 12 - Sun, Sep 21
DEN
Denver Intl.
ORD
O'Hare Intl.
$125 Roundtrip, found 19 hours ago
$125
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Fri, Sep 12 from Denver Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $125 found 19 hours ago
Frontier Airlines
Sat, Oct 11 - Wed, Oct 15
DEN
Denver Intl.
ORD
O'Hare Intl.
$128 Roundtrip, found 6 days ago
$128
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Oct 11 from Denver Intl. to O'Hare Intl., returning Wed, Oct 15, priced at $128 found 6 days ago
Frontier Airlines
Mon, Sep 29 - Wed, Oct 8
DEN
Denver Intl.
ORD
O'Hare Intl.
$131 Roundtrip, found 2 days ago
$131
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 29 from Denver Intl. to O'Hare Intl., returning Wed, Oct 8, priced at $131 found 2 days ago
Frontier Airlines
Sat, Oct 25 - Sun, Oct 26
DEN
Denver Intl.
MDW
Midway Intl.
$131 Roundtrip, found 1 day ago
$131
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Denver Intl. to Midway Intl., returning Sun, Oct 26, priced at $131 found 1 day ago
United
Fri, Oct 24 - Mon, Oct 27
DEN
Denver Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select United flight, departing Fri, Oct 24 from Denver Intl. to O'Hare Intl., returning Mon, Oct 27, priced at $169 found 1 day ago
American Airlines
Sat, Oct 25 - Sun, Oct 26
DEN
Denver Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 25 from Denver Intl. to O'Hare Intl., returning Sun, Oct 26, priced at $169 found 1 day ago
Delta
Sat, Nov 8 - Tue, Nov 11
DEN
Denver Intl.
MDW
Midway Intl.
$196 Roundtrip, found 14 hours ago
$196
Roundtrip
found 14 hours ago
Select Delta flight, departing Sat, Nov 8 from Denver Intl. to Midway Intl., returning Tue, Nov 11, priced at $196 found 14 hours ago
American Airlines
Fri, Oct 24 - Mon, Oct 27
DEN
Denver Intl.
RFD
Greater Rockford
$205 Roundtrip, found 1 day ago
$205
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct 24 from Denver Intl. to Greater Rockford, returning Mon, Oct 27, priced at $205 found 1 day 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 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 $98, 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 $98 right now, why wait?

Hillside Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$84

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 free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,973 reviews)
"The staff was fantastic—friendly, helpful, and attentive, which really made the stay more pleasant. The hotel itself, however, is clearly very old, and many features show their age. My room was small but nicely kept, and the lakeside view was absolutely stunning. The room door was very difficult ..."

Reviewed on Aug 13, 2025

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Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,851 reviews)
"Helpful staff, beautiful hotel in a great location!"

Reviewed on Aug 12, 2025

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Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (3,675 reviews)
"Very classy safe snd clean"

Reviewed on Aug 12, 2025

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Hilton Garden Inn Chicago Downtown/Magnificent Mile
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 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,688 reviews)
Nice Hotel With Great Location
"Great hotel in a very convenient location. Really close to Grand Red Line stop with plenty of places to eat. Not far from Magnificent Mile and Grant Park. Hotel is well kept, and the service is excellent. We did have an issue with our TV and phone. The first maintenance guy to show up could not fix ..."

Reviewed on Aug 13, 2025

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Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (3,568 reviews)
"N/a"

Reviewed on Aug 14, 2025

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citizenM Chicago Downtown
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 ...
8.8/10 Excellent! (2,635 reviews)
"I was pleasantly surprised to find this hotel so close in proximity to both the Mag Mile and Lake Shore Drive. Very walkable to downtown Chicago. I was disappointed to find scaffolding all over the one facade of the hotel - the facade through which you enter. I found the lobby and dining areas to ..."

Reviewed on Aug 15, 2025

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Hilton Chicago/Magnificent Mile Suites
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,183 reviews)
"Very nice place close to so many places."

Reviewed on Aug 15, 2025

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The Wade
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,191 reviews)
"Great place to stay when in Chicago the only thing is the parking sucks."

Reviewed on Aug 12, 2025

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InterContinental Chicago Magnificent Mile by IHG
See all 5,072 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
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! (1,001 reviews)
"Decent hotel. Staff were friendly and the service was quick. Although, no option for free continental breakfast that so many hotels offer these days."

Reviewed on Aug 13, 2025

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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 ...
6.8/10 (1,000 reviews)
"All was good."

Reviewed on Aug 11, 2025

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Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
See all 5,072 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.