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Highland

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Highland Flights as Low as $131

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

Frontier Airlines
Sat, Jul 18 - Tue, Jul 21
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$131 Roundtrip, found 3 days ago
$131
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jul 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jul 21, priced at $131 found 3 days ago
Frontier Airlines
Sat, Jul 18 - Tue, Jul 21
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jul 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jul 21, priced at $142 found 3 days ago
Frontier Airlines
Wed, Sep 16 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 6 hours ago
$148
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $148 found 6 hours ago
Frontier Airlines
Tue, Jul 7 - Tue, Jul 7
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$150 Roundtrip, found 4 days ago
$150
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Jul 7 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 7, priced at $150 found 4 days ago
Frontier Airlines
Tue, Aug 4 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 1 day ago
$152
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $152 found 1 day ago
United
Wed, Jul 1 - Tue, Aug 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jul 1 from Logan Intl. to O'Hare Intl., returning Tue, Aug 4, priced at $153 found 1 day ago
JetBlue Airways
Wed, Aug 26 - Tue, Sep 15
BOS
Logan Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Aug 26 from Logan Intl. to O'Hare Intl., returning Tue, Sep 15, priced at $157 found 6 days ago
Frontier Airlines
Mon, Aug 10 - Thu, Aug 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$158 Roundtrip, found 7 hours ago
$158
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Mon, Aug 10 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Aug 13, priced at $158 found 7 hours ago
Delta
Wed, Aug 12 - Sat, Aug 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 6 days ago
$172
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 22, priced at $172 found 6 days ago
American Airlines
Wed, Jul 1 - Wed, Aug 5
BOS
Logan Intl.
RFD
Greater Rockford
$191 Roundtrip, found 23 hours ago
$191
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Wed, Jul 1 from Logan Intl. to Greater Rockford, returning Wed, Aug 5, priced at $191 found 23 hours ago
Frontier Airlines
Fri, Jul 3 - Wed, Jul 8
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$218 Roundtrip, found 4 days ago
$218
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Jul 3 from San Francisco Intl. to O'Hare Intl., returning Wed, Jul 8, priced at $218 found 4 days ago
American Airlines
Wed, Jul 1 - Sat, Jul 4
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$245 Roundtrip, found 4 days ago
$245
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jul 1 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sat, Jul 4, priced at $245 found 4 days ago
Alaska Airlines
Sat, Oct 3 - Mon, Oct 5
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$249 Roundtrip, found 4 days ago
$249
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Sat, Oct 3 from San Francisco Intl. to O'Hare Intl., returning Mon, Oct 5, priced at $249 found 4 days ago
Frontier Airlines
Tue, Jun 30 - Sat, Jul 4
BOS
Logan Intl.
MDW
Midway Intl.
$291 Roundtrip, found 6 hours ago
$291
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Jun 30 from Logan Intl. to Midway Intl., returning Sat, Jul 4, priced at $291 found 6 hours ago
Sun Country Airlines
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$353 Roundtrip, found 17 hours ago
$353
Roundtrip
found 17 hours ago
Select Sun Country Airlines flight, departing Thu, Aug 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 23, priced at $353 found 17 hours ago
American Airlines
Fri, Jul 3 - Wed, Jul 15
SFO
San Francisco Intl.
RFD
Greater Rockford
$499 Roundtrip, found 1 day ago
$499
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jul 3 from San Francisco Intl. to Greater Rockford, returning Wed, Jul 15, priced at $499 found 1 day 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 $131, 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 $131 right now, why wait?

Highland Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$131

Last Minute Hotel Deals in Highland

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! (1,078 reviews)
"Overall not a bad experience. Just rooms need to be cleaned much better. More attention to detail"

Reviewed on Jun 4, 2026

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DoubleTree by Hilton Chicago - Alsip
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! (415 reviews)
"The stay was amazing. I would definitely recommend anyone to stay here while visiting Chicago. I do, however have some recommendations. Hotter water for the showers and microwaves for the rooms. If I am buying food from the hotel restaurants, and cannot finish it all, how am I to reheat my leftovers? ..."

Reviewed on Jun 6, 2026

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Wind Creek Southland Casino and Hotel
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 ...
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EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
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! (344 reviews)
"Nice"

Reviewed on Jun 5, 2026

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Motel 6 - Chicago, IL
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. ...
6.8/10 (1,007 reviews)
"It's more than I expected for what I paid. They haven't renovated the pool yet but the rooms are updated and nice. The staff was very friendly and incredibly helpful. You can cast to the TV's from your phone which was great. I could just use all my regular streaming apps. Close enough to downtown ..."

Reviewed on Jun 6, 2026

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Chicago Lake Shore Hotel
Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
12801 South Cicero Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (1,172 reviews)
"We stay at the Baymont Every time we come to visit! Staff is great! Breakfast is good ! I just wish the hallway towards the end of the hotel has a bad smell! That are just needs some TLC! Besides that one thing, it’s a 9 out of 10"

Reviewed on Jun 5, 2026

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Baymont by Wyndham Chicago/Alsip
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 (809 reviews)
"Okay!! hdbsjsbsbdbdbdjdjdndndbdbdbd"

Reviewed on Jun 1, 2026

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Econo Lodge South Holland - Chicago Southland
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! (1,008 reviews)
"Good hotel, everything was as expected. Staff very helpful and friendly."

Reviewed on Jun 3, 2026

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Hyatt Place Chicago-South/University Medical Center
See all 909 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.