$33 Cheap Flights to Highland, IN

View $33 flight on Tue, May 19, 2026Opens in a new window

Popular airlines to Highland

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How much is the cheapest flight to Highland?

Prices were available within the past 7 days and start at $33 for one-way flights and $72 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, May 19 - Tue, Jun 2
DFW
Dallas
MDW
Chicago
$83 Roundtrip, found 5 hours ago
$83
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, May 19 from Dallas to Chicago, returning Tue, Jun 2, priced at $83 found 5 hours ago
Spirit Airlines
Tue, May 5 - Wed, Jun 10
LGA
New York
ORD
Chicago
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, May 5 from New York to Chicago, returning Wed, Jun 10, priced at $118 found 2 days ago
American Airlines
Sat, Jul 4 - Tue, Jul 21
LGA
New York
RFD
Rockford
$176 Roundtrip, found 4 days ago
$176
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jul 4 from New York to Rockford, returning Tue, Jul 21, priced at $176 found 4 days ago
Delta
Mon, Jun 22 - Fri, Jun 26
LGA
New York
ORD
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Delta flight, departing Mon, Jun 22 from New York to Chicago, returning Fri, Jun 26, priced at $177 just found
United
Thu, Jul 23 - Tue, Jul 28
EWR
New York
ORD
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select United flight, departing Thu, Jul 23 from New York to Chicago, returning Tue, Jul 28, priced at $177 just found

Alternative airports near Highland

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Cheapest option available. Average driving time to city center is 39 minutes. Flights from $324
MDW
Midway Intl.
Cheapest
Average driving time to city center39 min
Flights from $324

Frequently asked questions

What month is the cheapest to fly to Highland?
The cheapest month to fly to Highland is May when demand is low. Off-peak months are usually when you'll find cheap flights. To keep costs down, avoid flying during school breaks and major holidays.
Which US cities have the cheapest flights to Highland?
Land cheap flights to Highland from New York, Washington and Dallas. These cities usually offer the best fares to this unique destination. But remember that seasonality, demand and stopovers will also have an influence on rates, so stay flexible and book when you see a bargain.
Which US cities fly direct to Highland?
Take your pick of 150 US cities with direct flights to Highland. While booking on Expedia, check "Direct flights only" to find nonstop itineraries. Fly to Highland from any of these top cities:

  • New York
  • Washington
  • Dallas
  • Boston
  • Phoenix

How to find a cheap flight to Highland?
If you're looking for cheap flights to Highland, consider low-season travel. Booking in advance may also save you money. Or, fly on a different day — flights on a Thursday are on average 16% cheaper than Sunday options.* Opt to receive flight price alerts on the Expedia app and get notifications as soon as fares fall.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Highland?
While booking in advance is typically the easiest way to save cash, don't panic if your Highland vacation is last minute. It's still possible to find cheap flights to Highland, especially if your plans have some flexibility. Try changing your trip dates, looking at different ticket types or flying out of an alternative airport.
How far in advance should I book a flight to Highland?
Book your flight to Highland two to four months ahead if you're jetting in from an international destination. For domestic travel, the timeframe is around 28 days in advance. Lower fares and a wider variety of travel dates, schedules and seating options are some of the great reasons to book early.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Highland?
Sundays are typically the best day to book a cheap flight to Highland, with savings of about 8% on average compared to Fridays. If you purchase tickets on a Friday, expect to spend more as this is often the most expensive day.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Highland?
Highland has connections to 216 airports worldwide through 44 airlines, with O'Hare Intl. Airport (ORD) as its chief gateway. Pick from these leading airlines to Highland when organizing your trip:

  • United Airlines
  • American Airlines
  • Delta Air Lines
  • Alaska Airlines

Where do you fly into Highland?
The main airport when you fly to Highland is Midway Intl. Airport (MDW), but there are other nearby options like Lewis University Airport (LOT) and O'Hare Intl. Airport (ORD). You can also land at Gary, IN (GYY-Gary - Chicago Intl.) and Valparaiso, IN (VPZ-Porter County Municipal) when flying to Highland.
How far is the airport from central Highland?
If you're arriving at Midway Intl. Airport (MDW), you'll be roughly 20 mi northwest of the center of Highland.
Can I save money by booking a Highland trip package?
Book a Highland flight and hotel package deal on Expedia, and you can benefit from significant savings. It's a breeze to bundle your flight and hotel, and you can add activities and car rentals to create your own customized Highland trip. Plus, nothing beats the convenience of booking everything in one place.
Can I change or cancel my flight to Highland?
If you booked your flight to Highland in the last 24 hours, you can often change or cancel it without fees. After that, additional costs may apply depending on the airline's terms and conditions. To learn more, check out our Customer Service Portal. Bear in mind that some flights are non-refundable, so you may be issued a credit toward a future trip rather than a direct refund. When browsing on Expedia, check the "Changes included" or "No cancel fee" boxes to see fares with flexible change policies.

*Flight schedules are subject to change.

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Travel information

Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
$72

Trending flights to Highland

Prices were available within the past 7 days and start at $33 for one-way flights and $72 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Jun 6 - Tue, Jun 9
ATL
Atlanta
MDW
Chicago
$72 Roundtrip, found 1 hour ago
$72
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Atlanta to Chicago, returning Tue, Jun 9, priced at $72 found 1 hour ago

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