Cheap flights To Highland (RFD) from $31

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 $31 One Way, $62 Round Trip

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

Mon, May 19 - Sun, May 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$62 Roundtrip, just found
$62
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, May 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, May 25, priced at $62 just found
Sat, May 31 - Wed, Jun 4
LGA
LaGuardia
ORD
O'Hare Intl.
$69 Roundtrip, found 3 hours ago
$69
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, May 31 from LaGuardia to O'Hare Intl., returning Wed, Jun 4, priced at $69 found 3 hours ago
Wed, May 7 - Wed, May 7
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$69 Roundtrip, found 6 days ago
$69
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, May 7 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, May 7, priced at $69 found 6 days ago
Fri, May 23 - Sun, May 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$75 Roundtrip, just found
$75
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, May 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, May 25, priced at $75 just found
Tue, May 20 - Tue, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$75 Roundtrip, found 6 days ago
$75
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, May 20 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jun 3, priced at $75 found 6 days ago
Sat, May 24 - Thu, May 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, just found
$76
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 24 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, May 29, priced at $76 just found
Thu, May 22 - Mon, May 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$78 Roundtrip, just found
$78
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, May 26, priced at $78 just found
Wed, Aug 6 - Wed, Aug 6
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$101 Roundtrip, found 20 hours ago
$101
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Wed, Aug 6 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Aug 6, priced at $101 found 20 hours ago
Sat, Jul 12 - Tue, Jul 15
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$106 Roundtrip, just found
$106
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jul 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $106 just found
Wed, May 14 - Tue, May 27
LGA
LaGuardia
ORD
O'Hare Intl.
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select United flight, departing Wed, May 14 from LaGuardia to O'Hare Intl., returning Tue, May 27, priced at $139 found 1 day ago

Highland ORD Flight Information

Traveling To
Highland
Destination Airport IATA Code
RFD
Number of Airlines Serving
16
Airlines
Spirit Airlines, Frontier Airlines, JetBlue Airways, Southwest Airlines, United
Flight Price
$62
Earliest Departing Flight
AA 3446 5:56AM EDT
Latest Departing Flight
IB 4838 May 8 6:46PM EDT

Book Your Flight & Hotel Together & Save

Highland economy flight packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Alsip, IL
2.0-star property

Motel 6 Alsip, IL

Jun 6 - Jun 9

3 night stay

New York (NYC) to Chicago (MDW)

American Airlines • Roundtrip • Coach
per person
found 1 day ago
Luxe Inn and Suites
2.5-star property

Luxe Inn and Suites

Jun 6 - Jun 9

3 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Roundtrip • Coach
per person
found 1 day ago
Club Quarters Hotel Wacker at Michigan, Chicago
4.0-star property

Club Quarters Hotel Wacker at Michigan, Chicago

Jun 27 - Jun 29

2 night stay

Baltimore (BWI) to Chicago (ORD)

Delta • Non-stop • Coach

Chicago (ORD) to Baltimore (BWI)

Spirit Airlines • Non-stop • Coach
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from New York to Highland
View all trips

Highland premium economy 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

8/10 Very Good! (1,524 reviews)

Jun 2 - Jun 5

3 night stay

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

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 1 day ago
Great location for doing things downtown. Walkable to every where one wants to go, or a cheap Lyft ride.

Reviewed on May 1, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (1,605 reviews)

Jun 2 - Jun 5

3 night stay

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

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 1 day ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,546 reviews)

Jun 2 - Jun 5

3 night stay

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

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 1 day ago
Loved their spa facility

Reviewed on Mar 21, 2025

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

Highland first class flight packages

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
4.0-star property

Arlo Chicago

9.2/10 Wonderful! (1,665 reviews)

Jun 13 - Jun 16

3 night stay

Washington (DCA) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Washington (DCA)

Delta • FirstClass
per person
just found
Nice hotel. Great location. Nice room. Pictures made hotel seem like it was so much more. It was just one small hallway. Nothing more. Very disappointed with the lobby. I thought by the pictures I was getting so much more! Payed a $150 resort fee for two night. There was absolutely no resort and no resort benefits. That was purely a money grab. Didn’t even get my room cleaned each day. Nice room. Nice hotel. Just less that I thought!

Reviewed on Oct 13, 2024

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (1,605 reviews)

Jun 13 - Jun 16

3 night stay

Washington (DCA) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Washington (DCA)

Delta • FirstClass
per person
just found
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Omni Chicago Hotel
4.5-star property

Omni Chicago Hotel

9/10 Wonderful! (1,444 reviews)

Jun 13 - Jun 16

3 night stay

Washington (DCA) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Washington (DCA)

Delta • FirstClass
per person
just found
Favorite place to stay whenever I’m in Chicago!

Reviewed on Dec 28, 2024

Don't see what you're looking for?
See all available trips from Washington 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 $62 and $139 for a round-trip flight to Highland. Tickets one-way originating from Atlanta (ATL) dropped to just $31 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.

Nearby

Flights To

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.