Search Cheap Flights to
Highland

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Highland Flights as Low as $70

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

Frontier Airlines
Tue, May 12 - Tue, May 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$70 Roundtrip, found 1 day ago
$70
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, May 19, priced at $70 found 1 day ago
Frontier Airlines
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 13 hours ago
$76
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $76 found 13 hours ago
Frontier Airlines
Thu, Apr 30 - Thu, May 7
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$161 Roundtrip, found 5 days ago
$161
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, May 7, priced at $161 found 5 days ago
Frontier Airlines
Mon, Apr 27 - Thu, Apr 30
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Charlotte-Douglas Intl. to O'Hare Intl., returning Thu, Apr 30, priced at $164 found 1 day ago
Bargain Flight
Wed, May 13 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, May 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $165 found 1 day ago
Bargain Flight
Wed, May 6 - Sat, May 30
BNA
Nashville Intl.
ORD
O'Hare Intl.
$175 Roundtrip, found 19 hours ago
$175
Roundtrip
found 19 hours ago
Select Bargain Flight flight, departing Wed, May 6 from Nashville Intl. to O'Hare Intl., returning Sat, May 30, priced at $175 found 19 hours ago
Spirit Airlines
Sat, May 16 - Tue, May 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 2 days ago
$178
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, May 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 19, priced at $178 found 2 days ago
Frontier Airlines
Tue, May 12 - Sat, May 30
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$185 Roundtrip, found 5 days ago
$185
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, May 12 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Sat, May 30, priced at $185 found 5 days ago
American Airlines
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 13 hours ago
$197
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $197 found 13 hours ago
Delta
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 13 hours ago
$197
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $197 found 13 hours ago
Contour Airlines
Wed, Jun 10 - Mon, Jun 22
BNA
Nashville Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 19 hours ago
$217
Roundtrip
found 19 hours ago
Select Contour Airlines flight, departing Wed, Jun 10 from Nashville Intl. to O'Hare Intl., returning Mon, Jun 22, priced at $217 found 19 hours ago
American Airlines
Tue, May 26 - Tue, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
RFD
Greater Rockford
$233 Roundtrip, found 2 days ago
$233
Roundtrip
found 2 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 $233 found 2 days ago
American Airlines
Fri, May 15 - Mon, May 18
CLT
Charlotte-Douglas Intl.
RFD
Greater Rockford
$265 Roundtrip, found 4 days ago
$265
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, May 15 from Charlotte-Douglas Intl. to Greater Rockford, returning Mon, May 18, priced at $265 found 4 days ago
Delta
Tue, Sep 8 - Tue, Sep 15
CLT
Charlotte-Douglas Intl.
MDW
Midway Intl.
$279 Roundtrip, found 13 hours ago
$279
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Sep 8 from Charlotte-Douglas Intl. to Midway Intl., returning Tue, Sep 15, priced at $279 found 13 hours ago
American Airlines
Thu, May 14 - Mon, May 18
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$304 Roundtrip, found 1 day ago
$304
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, May 14 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Mon, May 18, priced at $304 found 1 day ago
American Airlines
Wed, May 6 - Sat, May 30
BNA
Nashville Intl.
RFD
Greater Rockford
$467 Roundtrip, found 18 hours ago
$467
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Wed, May 6 from Nashville Intl. to Greater Rockford, returning Sat, May 30, priced at $467 found 18 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 May, 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 14 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 $70, 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 $70 right now, why wait?

Highland Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$70

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 ...
6/10 (763 reviews)
Right off toll road...shopping and eateries on other side if interstate...best price also in that area

Reviewed on Apr 18, 2026

Get rates
Econo Lodge South Holland - Chicago Southland
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! (1,021 reviews)
Yes, I felt safe walking to and from my car. The room was very comfortable and clean. I didn't have the breakfast, I've heard its good.

Reviewed on Apr 26, 2026

Get rates
DoubleTree by Hilton Chicago - Alsip
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 (1,001 reviews)
The outside area was okay. The inside was clean, bed was comfortable. There was a microwave (didn’t use) and refrigerator. Large screen tv was nice. Water pressure was just okay. Had some issues checking in because I used my initials (which is what I go by) on my reservation and my ID has my name ...

Reviewed on Apr 21, 2026

Get rates
Chicago Lake Shore Hotel
Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave Oak Lawn IL
Book a stay at this business-friendly hotel in Oak Lawn. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,306 reviews)
Staff was nice.

Reviewed on Apr 26, 2026

Get rates
Hilton Chicago/Oak Lawn
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! (343 reviews)
The staff provided Excellent customer service!!

Reviewed on Apr 25, 2026

Get rates
Wind Creek Southland Casino and Hotel
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! (302 reviews)
I did find two active roaches in the bathroom everything else including sheets and ac was fine

Reviewed on Apr 25, 2026

Get rates
Motel 6 - Chicago, IL
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! (1,267 reviews)
Clean rooms, several visits to same room! Love it.

Reviewed on Apr 24, 2026

Get rates
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
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! (1,097 reviews)
We stay here often. Always clean and staff friendly. I like that you get fresh towels each day and your room is straightened up by housekeeping. The breakfast is. The same as other hotels. They have waffles biscuits with gravy and a variety of cereals. Yogurt and raisin toast is my usual. Coffee ...

Reviewed on Apr 26, 2026

Get rates
Baymont by Wyndham Chicago/Alsip
See all 925 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.