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Highland

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Highland Flights as Low as $111

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

Frontier Airlines
Tue, Jul 21 - Sat, Jul 25
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$111 Roundtrip, found 5 days ago
$111
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Jul 21 from George Bush Intercontinental to O'Hare Intl., returning Sat, Jul 25, priced at $111 found 5 days ago
Frontier Airlines
Wed, Sep 30 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$138 Roundtrip, found 9 hours ago
$138
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Sep 30 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 30, priced at $138 found 9 hours ago
Frontier Airlines
Wed, Oct 21 - Tue, Nov 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 6 hours ago
$138
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Nov 10, priced at $138 found 6 hours ago
United
Tue, Sep 1 - Tue, Sep 15
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$171 Roundtrip, found 13 hours ago
$171
Roundtrip
found 13 hours ago
Select United flight, departing Tue, Sep 1 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Sep 15, priced at $171 found 13 hours ago
American Airlines
Tue, Aug 25 - Sat, Sep 5
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$187 Roundtrip, found 5 days ago
$187
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Aug 25 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Sep 5, priced at $187 found 5 days ago
Delta
Tue, Sep 1 - Tue, Sep 15
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$191 Roundtrip, found 13 hours ago
$191
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Sep 1 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Sep 15, priced at $191 found 13 hours ago
Frontier Airlines
Wed, Aug 5 - Tue, Aug 18
IAH
George Bush Intercontinental
MDW
Midway Intl.
$215 Roundtrip, just found
$215
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Aug 5 from George Bush Intercontinental to Midway Intl., returning Tue, Aug 18, priced at $215 just found
JetBlue Airways
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$279 Roundtrip, found 9 hours ago
$279
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $279 found 9 hours ago
American Airlines
Fri, Jul 24 - Fri, Jul 31
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$285 Roundtrip, found 9 hours ago
$285
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Fri, Jul 24 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, Jul 31, priced at $285 found 9 hours ago
Frontier Airlines
Tue, Aug 11 - Wed, Nov 11
MEX
Mexico City Intl.
ORD
O'Hare Intl.
$305 Roundtrip, found 9 hours ago
$305
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Mexico City Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $305 found 9 hours ago
American Airlines
Fri, Jul 3 - Sat, Jul 11
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$317 Roundtrip, found 5 days ago
$317
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Jul 3 from Newark Liberty Intl. Airport to Greater Rockford, returning Sat, Jul 11, priced at $317 found 5 days ago
Frontier Airlines
Sat, Jul 4 - Wed, Jul 8
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$350 Roundtrip, found 1 day ago
$350
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jul 4 from Newark Liberty Intl. Airport to Midway Intl., returning Wed, Jul 8, priced at $350 found 1 day ago
Volaris
Mon, Sep 21 - Mon, Oct 5
NLU
Felipe Ángeles Intl.
ORD
O'Hare Intl.
$357 Roundtrip, found 9 hours ago
$357
Roundtrip
found 9 hours ago
Select Volaris flight, departing Mon, Sep 21 from Felipe Ángeles Intl. to O'Hare Intl., returning Mon, Oct 5, priced at $357 found 9 hours ago
Viva
Mon, Sep 21 - Mon, Oct 5
TLC
Toluca Intl.
ORD
O'Hare Intl.
$406 Roundtrip, found 9 hours ago
$406
Roundtrip
found 9 hours ago
Select Viva flight, departing Mon, Sep 21 from Toluca Intl. to O'Hare Intl., returning Mon, Oct 5, priced at $406 found 9 hours ago
Aeromexico
Mon, Aug 10 - Tue, Nov 10
MEX
Mexico City Intl.
MDW
Midway Intl.
$455 Roundtrip, found 9 hours ago
$455
Roundtrip
found 9 hours ago
Select Aeromexico flight, departing Mon, Aug 10 from Mexico City Intl. to Midway Intl., returning Tue, Nov 10, priced at $455 found 9 hours ago
Volaris
Wed, Aug 12 - Wed, Aug 12
TLC
Toluca Intl.
MDW
Midway Intl.
$564 Roundtrip, found 9 hours ago
$564
Roundtrip
found 9 hours ago
Select Volaris flight, departing Wed, Aug 12 from Toluca Intl. to Midway Intl., returning Wed, Aug 12, priced at $564 found 9 hours ago

Cheap Flights to Highland

Fall in love at first flight with your vacation to Highland 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 Highland on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Highland, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Highland

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Highland 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 RFD airport.

What is the cheapest month to fly to Highland?

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 Highland are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Highland?

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 Highland.

What airport is best to fly into Highland?

When you’re planning your trip to Highland, convenience is the name of the game. Luckily, Highland Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Highland must-do list.

How much are flights to Highland?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Highland on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $111, 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 Highland?

The trick to saving a stack of cash on your flight to Highland? 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 $111 right now, why wait?

Highland Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$122

Last Minute Hotel Deals in Highland

Econo Lodge South Holland - Chicago Southland

Econo Lodge South Holland - Chicago Southland

2 out of 5
17301 S Halsted St, Building B South Holland IL
Stay at this hotel in South Holland. Enjoy free WiFi, free parking, and room service. Popular attractions Midwest Carvers Museum and Harvey Public Library are ...
6.2/10 (822 reviews)
"Needs to fix WiFi asap and need coffee pot in room"

Reviewed on Jun 28, 2026

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Econo Lodge South Holland - Chicago Southland
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street Chicago IL
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Abbott Park and Martin Luther King Drive are located ...
7.4/10 Good! (377 reviews)
"This hotel is a great value. Most were charging double or triple this price. My only complaint is the noise from the street. It's not very soundproof. The staff were wonderful. I would stay here again. Oh yeah, the parking is free. You don't find that often in Chicago. A security guard is present ..."

Reviewed on Jun 28, 2026

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Motel 6 - Chicago, IL
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
17300 S Halsted St Hazel Crest IL
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe ...
9.4/10 Exceptional! (464 reviews)
"Helpful staff and clean facility. Don’t plan on sleeping! Very loud neighbors, partying, music, arguments, multiple people in and out of the room, until 4 AM. No security, or staff, walking the hallways. They are only in the casino."

Reviewed on Jun 29, 2026

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Wind Creek Southland Casino and Hotel
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,108 reviews)
"Great stay, quiet and staff was very friendly. Also, the breakfast buffet was good."

Reviewed on Jun 27, 2026

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DoubleTree by Hilton Chicago - Alsip
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

3.5 out of 5
18501 Convention Center Drive Tinley Park IL
Book a stay at this business-friendly hotel in Tinley Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,369 reviews)
"Good overall. Clean. The elevator is a little bit creepy needs to be repaired."

Reviewed on Jun 28, 2026

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EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. ...
7/10 Good! (1,014 reviews)
"The hotel is a little aged but the room was clean and the location was fine. The staff was nice."

Reviewed on Jun 28, 2026

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Chicago Lake Shore Hotel
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

3 out of 5
5225 S Harper Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (1,003 reviews)
"Wow! What a great experience this was. I love how when I walked in the hotel I immediately saw smiling faces and a poster of President Obama in the corner. It was right on brand for my stay as I was visiting the Obama Presidential Center for the Grand Opening weekend. The breakfast was delicious ..."

Reviewed on Jun 25, 2026

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Hyatt Place Chicago-South/University Medical Center
Quality Inn & Suites Orland Park - Chicago

Quality Inn & Suites Orland Park - Chicago

2.5 out of 5
8800 W 159th St Orland Park IL
Book a stay at this business-friendly hotel in Orland Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.4/10 Good! (1,003 reviews)
"Good place to stay for a night. Needs to be updated"

Reviewed on Jun 28, 2026

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Quality Inn & Suites Orland Park - Chicago
See all 912 properties in Highland
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.