Cheap flights To Highland (RFD) from $29

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Cheap Flights to Highland from $29 One Way, $58 Round Trip

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

Sat, Feb 21 - Sat, Feb 28
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$58 Roundtrip, found 19 hours ago
$58
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Feb 28, priced at $58 found 19 hours ago
Sat, Feb 14 - Sat, Feb 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$59 Roundtrip, just found
$59
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Feb 14 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Feb 21, priced at $59 just found
Mon, Jan 12 - Sun, Jan 18
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$74 Roundtrip, just found
$74
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Jan 12 from Raleigh - Durham Intl. to O'Hare Intl., returning Sun, Jan 18, priced at $74 just found
Tue, Jan 6 - Tue, Jan 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 3 days ago
$87
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Jan 6 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Jan 6, priced at $87 found 3 days ago
Tue, Feb 10 - Tue, Feb 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 4 days ago
$108
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Feb 10 from Los Angeles Intl. to O'Hare Intl., returning Tue, Feb 17, priced at $108 found 4 days ago
Sat, Jan 24 - Mon, Feb 2
BOS
Logan Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Jan 24 from Logan Intl. to O'Hare Intl., returning Mon, Feb 2, priced at $127 found 4 days ago
Sat, Jan 17 - Mon, Jan 26
BOS
Logan Intl.
ORD
O'Hare Intl.
$133 Roundtrip, found 5 days ago
$133
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Jan 17 from Logan Intl. to O'Hare Intl., returning Mon, Jan 26, priced at $133 found 5 days ago
Thu, Jan 15 - Tue, Jan 20
BOS
Logan Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select United flight, departing Thu, Jan 15 from Logan Intl. to O'Hare Intl., returning Tue, Jan 20, priced at $134 found 1 day ago
Tue, Jan 20 - Fri, Jan 23
BOS
Logan Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 20 from Logan Intl. to O'Hare Intl., returning Fri, Jan 23, priced at $134 found 1 day ago
Tue, Jan 20 - Fri, Jan 23
BOS
Logan Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jan 20 from Logan Intl. to O'Hare Intl., returning Fri, Jan 23, priced at $134 found 1 day ago

Highland Flight Information

Traveling To
Highland
Destination Airport IATA Code
RFD
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Southwest Airlines, United, American Airlines, Delta, JetBlue Airways
Flight Price
$58
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Highland economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago Downtown
4.0-star property

The Royal Sonesta Chicago Downtown

Feb 10 - Feb 13

3 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $354, price is now $237 per person
$237
per person
found 1 day ago
Arlo Chicago
4.0-star property

Arlo Chicago

Feb 10 - Feb 13

3 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $354, price is now $241 per person
$241
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Feb 6 - Feb 8

2 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $662, price is now $454 per person
$454
per person
found 1 day ago
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See all available trips from Atlanta to Highland
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Highland premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (2,008 reviews)

Jan 16 - Jan 19

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $630, price is now $513 per person
$513
per person
found 15 hours ago
Solid place to stay

Reviewed on Nov 5, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Jan 16 - Jan 19

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $1,073, price is now $816 per person
$816
per person
found 16 hours ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,229 reviews)

Jan 16 - Jan 19

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $962, price is now $747 per person
$747
per person
found 16 hours ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

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Highland

Finding cheap flights to Highland is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Highland flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Highland through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Highland—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Highland flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Highland with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

Frequently asked questions

Which airlines fly to Highland?
With 20 airlines to select from, finding the perfect flight to match your itinerary and budget will be a piece of cake. O'Hare Intl. Airport (ORD) is the main gateway to Highland and where you'll likely be touching down. These popular international carriers are waiting to take you there:

  • United Airlines - 612 flights to Highland per month
  • American Airlines - 339 flights to Highland per month
  • Air Canada - 190 flights to Highland per month

What is the best airport to fly to in Highland?
Midway Intl. Airport (MDW). It's the city's main terminal and is located roughly 20 miles northwest of the center. You'll be unpacking your belongings and discovering the best of Highland shortly after landing.
How much is a flight to Highland?
This week, prices hovered between $58 and $134 for a round-trip flight to Highland. Tickets one-way originating from Dallas (DFW) dropped to just $29 over the same time period.
How to book the cheapest flight to Highland?
Using Orbitz, you'll find some of the best flight deals around from a big selection of airlines. But if you're eager to boost your prospects of scoring cheap flights to Highland, here are some pointers designed to help:

  • Consider taking off from or landing at nearby airports to save money. Enter your preferred departure and arrival airports in the form fields, then click on the 'Nearby airports' function below. It will show you any available options.
  • If you're flexible with when you take off, click on the 'Show flexible dates' option. You'll see the flight deals for the days either side of your chosen departure. Ticket prices often vary depending on what day it is.
  • You can also hit the 'Show options' link to filter results for your preferred carrier, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you'd prefer to fly.
  • Once you've figured out your travel dates, lock in your flight. Ticket prices usually climb as the departure date gets closer.
  • Think about combining your flights, hotels and car rental into an Orbitz package deal to stretch your budget even further.
  • Flying during busier seasons means costly airfares. Try to plan your vacation outside of popular dates, such as Thanksgiving, New Year's Eve and Easter.

How long is a flight to Highland?
You might have time to read a couple of chapters of a book, or you might plow through the whole thing! How long a flight is depends on where you're jetting out of, but these popular routes to Highland will give you an idea:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Midway Intl. Airport (MDW) - 1 hour and 51 minutes
  • Las Vegas, NV (LAS-Harry Reid Intl.) to Midway Intl. Airport (MDW) - 3 hours and 15 minutes
  • Orlando, FL (MCO-Orlando Intl.) to Midway Intl. Airport (MDW) - 2 hours and 40 minutes

What is the best time to book a flight to Highland?
If your schedule allows, book your seats to Highland in January. This is the best month to get low airfares, followed by February and August. With a bit of patience and planning, you're bound to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Highland?
In general, Tuesdays, Wednesdays and Saturdays are the cheapest days to book a flight to Highland. If you're looking for the most competitive airfares, search across those days and you could land an excellent flight deal.
What is the cheapest day of the week to fly to Highland?
Everyone enjoys a good bargain, so we suggest setting off early in the week for cheap flights to Highland. Orbitz data from 2020 shows you can snap up the best deals on flights that leave on Mondays. Tuesdays are the next most affordable day, while Saturdays are likely to cost a bundle. Many people like to start their trip when the working week is over, so leave those Saturdays for binge-watching your favorite TV shows.
What is the cheapest month to fly to Highland?
We won't keep you in suspense — according to Orbitz data, August is generally the most inexpensive month to fly. Ideal for those who need a weekend getaway or just a break from it all before the weather turns. Be aware that the least affordable time to fly is the height of summer, with ticket prices peaking in June.
Which airlines allow free cancellation?
We understand that plans can change and flexibility is important. That's why you can easily search for flights that include free cancellation and no change fees on Orbitz. Simply click on "Filter by flexible change policies" and we'll find you fares more flexible than a crayon left in the sun!
What do I need for the flight to Highland?
There's nothing more exciting than jetting off to a cool new place, but it's smart to be prepared. This list of handy tips will help get your journey off to a flying start:

  • Before you step on to the plane, you'll need to show proof of identification, such as your passport. You'll also need your ticket. If you're traveling with the kids, check with your airline about which documents they require — if any.
  • Take some activities to keep you occupied on your journey to Highland. Books, magazines and electronic devices like laptops and e-readers are good ideas. Remember to take a water bottle as well. Even on a short flight, it's important to stay well-hydrated.
  • Whatever the temperature is doing outside, plane cabins can get seriously cold. Bring a hoodie on board to keep yourself comfy.

How many direct flights are there to Highland?
There are 604 flights that head straight to Highland each month, so you won't have to stress over tiresome stopovers. Book a fare with Southwest Airlines or Frontier Airlines and then settle back, relax and enjoy the journey. Delta Air Lines, Volaris, Porter Airlines and Allegiant Air also offer nonstop flights to Highland.
How do I get cheap first-class/business deals to Highland?
Experienced travelers have a knack for finding first or business-class flights to Highland without the sky-high price tag. Follow their example with these helpful tips:

  • Flexibility doesn't just help with your yoga. Avoid locking in your travel dates so you can pick up cheaper airfares when a big sale drops.
  • Low-cost airlines offer first or business-class seats at affordable prices. Skip the full-service carriers and look into these cheaper options.
  • Bid for an upgrade in online auctions or upgrade your fare through your flight loyalty scheme.

How to get into Highland from the airport?
Make things more convenient with a Midway Intl. Airport (MDW) car rental. Arrive at Midway Intl. Airport (MDW) and then collect a ride from one of the two outlets on-site. Budget and Avis both have a great range of vehicles to choose from. Once you've thrown your bags in the trunk, you'll need to drive roughly 20 miles to the southeast to reach the hustle and bustle of central Highland. Renting a vehicle from downtown is another popular option with our Highland car rentals.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.