Cheap flights To Highland (RFD) from $28

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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.

Thu, May 14 - Mon, May 18
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$56 Roundtrip, found 3 hours ago
$56
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, May 14 from Sky Harbor Intl. to Midway Intl., returning Mon, May 18, priced at $56 found 3 hours ago
Thu, Mar 5 - Sat, Mar 7
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Mar 5 from Sky Harbor Intl. to O'Hare Intl., returning Sat, Mar 7, priced at $56 just found
Tue, May 19 - Wed, May 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, May 19 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 20, priced at $88 just found
Wed, Jun 3 - Sat, Jun 6
BOS
Logan Intl.
ORD
O'Hare Intl.
$94 Roundtrip, found 1 day ago
$94
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jun 3 from Logan Intl. to O'Hare Intl., returning Sat, Jun 6, priced at $94 found 1 day ago
Tue, Mar 10 - Tue, Mar 10
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$99 Roundtrip, found 15 hours ago
$99
Roundtrip
found 15 hours ago
Select United flight, departing Tue, Mar 10 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, Mar 10, priced at $99 found 15 hours ago
Mon, Apr 27 - Wed, Apr 29
BOS
Logan Intl.
MDW
Midway Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Apr 27 from Logan Intl. to Midway Intl., returning Wed, Apr 29, priced at $107 found 1 day ago
Tue, Jun 2 - Tue, Jun 9
BOS
Logan Intl.
ORD
O'Hare Intl.
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Jun 2 from Logan Intl. to O'Hare Intl., returning Tue, Jun 9, priced at $107 found 2 days ago
Tue, Mar 17 - Tue, Mar 17
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 10 hours ago
$109
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Mar 17 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Tue, Mar 17, priced at $109 found 10 hours ago
Tue, Mar 31 - Tue, Apr 7
BOS
Logan Intl.
ORD
O'Hare Intl.
$116 Roundtrip, found 11 hours ago
$116
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Mar 31 from Logan Intl. to O'Hare Intl., returning Tue, Apr 7, priced at $116 found 11 hours ago
Tue, May 5 - Wed, May 6
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$117 Roundtrip, found 6 days ago
$117
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, May 5 from Minneapolis - St. Paul Intl. to Midway Intl., returning Wed, May 6, priced at $117 found 6 days ago

Highland Flight Information

Traveling To
Highland
Destination Airport IATA Code
RFD
Number of Airlines Serving
Airlines
Frontier Airlines, Delta, American Airlines, Southwest Airlines, Spirit Airlines, JetBlue Airways, United
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.
Kinzie Hotel
4.0-star property

Kinzie Hotel

Mar 22 - Mar 27

5 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $706, price is now $477 per person
$477
per person
found 1 day ago
La Banque Hotel
4.0-star property

La Banque Hotel

Apr 3 - Apr 8

5 night stay

Atlanta (ATL) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Atlanta (ATL)

Frontier Airlines • Coach
Save 100% on your flight
Price was $979, price is now $650 per person
$650
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Mar 25 - Mar 29

4 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,382, price is now $929 per person
$929
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Atlanta to Highland
View all trips

Highland premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Wyndham Garden Kankakee
3.0-star property

Wyndham Garden Kankakee

8.4/10 Very Good! (895 reviews)

Apr 6 - Apr 9

3 night stay

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

Delta • Non-stop • PremiumEconomy

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

United • Non-stop • PremiumEconomy
Price was $628, price is now $583 per person
$583
per person
found 19 hours ago
Very professional young man checked us in. Facility is us just off interstate. So nice place

Reviewed on Nov 2, 2022

La Banque Hotel
4.0-star property

La Banque Hotel

9.4/10 Exceptional! (447 reviews)

Apr 6 - Apr 9

3 night stay

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

Delta • Non-stop • PremiumEconomy

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

United • Non-stop • PremiumEconomy
Price was $827, price is now $698 per person
$698
per person
found 19 hours ago
Beautiful boutique hotel with great staff!

Reviewed on Sep 16, 2022

Wind Creek Southland Casino and Hotel
4.0-star property

Wind Creek Southland Casino and Hotel

9.4/10 Exceptional! (160 reviews)

Apr 6 - Apr 9

3 night stay

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

Delta • Non-stop • PremiumEconomy

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

United • Non-stop • PremiumEconomy
Price was $727, price is now $672 per person
$672
per person
found 19 hours ago
Love the Cleanliness, and no smoking rooms. The staff was excellent! We will attend again

Reviewed on Nov 17, 2025

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

Price found within the past 48 hours. Click for updated prices.
Hyatt Centric Chicago Magnificent Mile
4.0-star property

Hyatt Centric Chicago Magnificent Mile

9/10 Wonderful! (1,034 reviews)

Mar 29 - Apr 1

3 night stay

Austin (AUS) to Chicago (ORD)

United • Non-stop • FirstClass

Chicago (ORD) to Austin (AUS)

Spirit Airlines • Non-stop • FirstClass
Price was $789, price is now $729 per person
$729
per person
found 17 hours ago
Room design, checking nd check out experience, general cleanliness etc

Reviewed on Feb 10, 2026

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,000 reviews)

Mar 29 - Apr 1

3 night stay

Austin (AUS) to Chicago (ORD)

United • Non-stop • FirstClass

Chicago (ORD) to Austin (AUS)

Spirit Airlines • Non-stop • FirstClass
Price was $1,348, price is now $1,060 per person
$1,060
per person
found 17 hours ago
Lovely room and spacious bathroom plus all of the high end touches (robes, slippers to soft mats and towels and great bath products and loved the nespresso maker!) View was not great but gym and lobby made up for it; bar was too crowded and we couldn’t get a late checkout but at least it was noon and they held our bags for a few hours!

Reviewed on Dec 31, 2025

The Ritz-Carlton, Chicago
5.0-star property

The Ritz-Carlton, Chicago

9.2/10 Wonderful! (1,002 reviews)

Mar 29 - Apr 1

3 night stay

Austin (AUS) to Chicago (ORD)

United • Non-stop • FirstClass

Chicago (ORD) to Austin (AUS)

Spirit Airlines • Non-stop • FirstClass
Price was $1,179, price is now $1,110 per person
$1,110
per person
found 17 hours ago
Best place in the city of Chicago to stay at

Reviewed on Dec 1, 2024

Don't see what you're looking for?
See all available trips from Austin to Highland
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Highland

Orbitz makes it easy for you to find cheap prices for flights to Highland. When you search for your tickets on Orbitz, you don’t have to look any further for the best Highland flights available ever again.

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Orbitz understands that your travel plans may change. That’s why we make it simple to cancel your ticket for Highland flights if necessary. All you have to do is contact the Orbitz Customer Service department to adjust your travel plans after booking. When you’re ready book your trip, just do a fresh search for the perfect flights to Highland again.

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Low Prices for Highland Flights

Orbitz has the scoop on cheap tickets and bargain airfare for flights to Highland. You can research the best flights for your trip and make your reservations all on our website with the confidence that you’re getting a great price.

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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 $117 for a round-trip flight to Highland. Tickets one-way originating from Phoenix (PHX) 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.