Cheap flights To Highland (RFD) from $28

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Highland from $28 One Way, $56 Round Trip

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

Sat, Apr 25 - Sun, Apr 26
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$56 Roundtrip, found 23 hours ago
$56
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Apr 25 from Newark Liberty Intl. Airport to Midway Intl., returning Sun, Apr 26, priced at $56 found 23 hours ago
Tue, May 5 - Wed, May 13
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$56 Roundtrip, found 1 day ago
$56
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, May 13, priced at $56 found 1 day ago
Mon, Apr 27 - Tue, Apr 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$69 Roundtrip, found 1 day ago
$69
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Apr 28, priced at $69 found 1 day ago
Thu, Apr 23 - Thu, Apr 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$73 Roundtrip, just found
$73
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Apr 23 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Apr 30, priced at $73 just found
Tue, Apr 14 - Tue, Apr 28
LGA
LaGuardia
ORD
O'Hare Intl.
$87 Roundtrip, found 2 hours ago
$87
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Apr 14 from LaGuardia to O'Hare Intl., returning Tue, Apr 28, priced at $87 found 2 hours ago
Fri, Apr 10 - Thu, Apr 16
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$99 Roundtrip, found 10 hours ago
$99
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Fri, Apr 10 from Newark Liberty Intl. Airport to O'Hare Intl., returning Thu, Apr 16, priced at $99 found 10 hours ago
Sat, Apr 25 - Tue, May 5
LGA
LaGuardia
MDW
Midway Intl.
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Apr 25 from LaGuardia to Midway Intl., returning Tue, May 5, priced at $144 found 1 day ago
Wed, May 13 - Tue, May 19
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 1 day ago
$152
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 13 from John F. Kennedy Intl. to O'Hare Intl., returning Tue, May 19, priced at $152 found 1 day ago
Wed, Apr 29 - Wed, Apr 29
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Apr 29 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $160 found 1 day ago
Tue, May 26 - Wed, May 27
LGA
LaGuardia
ORD
O'Hare Intl.
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, May 26 from LaGuardia to O'Hare Intl., returning Wed, May 27, priced at $162 found 1 day ago

Highland Flight Information

Traveling To
Highland
Destination Airport IATA Code
RFD
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, American Airlines, Southwest Airlines, JetBlue Airways, Delta
Flight Price
$56
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.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

May 8 - May 10

2 night stay

Dallas (DAL) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Price was $711, price is now $500 per person
$500
per person
found 1 day ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

May 23 - May 26

3 night stay

Dallas (DFW) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $909, price is now $675 per person
$675
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Dallas to Highland
View all trips

Highland first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,582 reviews)

May 15 - May 18

3 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,495, price is now $1,242 per person
$1,242
per person
found 17 hours ago
The rooms were clean and smelled fresh.

Reviewed on Jan 8, 2026

Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

9/10 Wonderful! (3,314 reviews)

May 15 - May 18

3 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,580, price is now $1,298 per person
$1,298
per person
found 17 hours ago
In convenient area either by walking or uber

Reviewed on Oct 18, 2025

Arlo Chicago
4.0-star property

Arlo Chicago

9.4/10 Exceptional! (2,019 reviews)

May 15 - May 18

3 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,827, price is now $1,593 per person
$1,593
per person
found 17 hours ago
The stay in ARLO hotel Chicago was very pleasant. The room was clean and warm. The staff was very helpful and friendly. I would recommend ARLO hotel Chicago to everyone who is planning to visit Chicago. Thank you.

Reviewed on Jan 25, 2026

Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Highland
View all trips

Highland

Save more on flights to Highland while making top-quality travel arrangements. At Orbitz we provide access to low cost flights, hotel lodgings and other discounts, along with superior customer service and an unbeatable satisfaction guarantee.

Compare And Book Discount Flights to Highland

Now it is easier than ever to find a discount Highland flight. Orbitz users can compare airfares for both international and domestic flights and can quickly determine the best hotels and car rental companies to use. You may also check out hotel and other reviews along with a number of travel tips, making your visit to an unfamiliar destination enjoyable and hassle-free.

Use Your Mobile Phone To Secure A Low Cost Flight To Highland

We now offer free apps for the most commonly used mobile devices. You can use your mobile phone to share relevant information pertaining to your trips, view images of local lodgings and take advantage of hotel and car rental discounts that may be available only to mobile device users.

Boost Your Frequent Flyer Rewards

You even retain your ability to earn frequent flier points and rewards when purchasing your tickets with Orbitz for Highland flights. Enter your frequent flyer information into your Orbitz profile to start earning rewards.

You will find that Orbitz is a very low cost, yet very effective travel planner. Free updates via your mobile phone device will help to keep you and all relevant parties informed of important flight updates. With access to unbeatable sales on all travel essentials, Orbitz makes booking an affordable flight to Highland a breeze.

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 $56 and $162 for a round-trip flight to Highland. Tickets one-way originating from New York (EWR) dropped to just $28 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.