Cheap flights To Highland (RFD) from $29

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Cheap Flights to Highland from $29 One Way, $56 Round Trip

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

Wed, Apr 22 - Mon, Apr 27
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$56 Roundtrip, found 11 hours ago
$56
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Newark Liberty Intl. Airport to Midway Intl., returning Mon, Apr 27, priced at $56 found 11 hours ago
Sat, Apr 25 - Mon, Apr 27
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$59 Roundtrip, found 1 hour ago
$59
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Apr 25 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Apr 27, priced at $59 found 1 hour ago
Sat, Apr 18 - Wed, Apr 22
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$66 Roundtrip, found 6 days ago
$66
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Apr 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Apr 22, priced at $66 found 6 days ago
Tue, May 5 - Mon, May 11
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$69 Roundtrip, found 8 hours ago
$69
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Mon, May 11, priced at $69 found 8 hours ago
Tue, May 26 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$70 Roundtrip, found 23 hours ago
$70
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue, May 26 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $70 found 23 hours ago
Wed, Apr 22 - Wed, Apr 22
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 2 days ago
$72
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Apr 22, priced at $72 found 2 days ago
Mon, Apr 13 - Sat, Apr 18
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$99 Roundtrip, found 2 days ago
$99
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Mon, Apr 13 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Apr 18, priced at $99 found 2 days ago
Wed, May 27 - Fri, May 29
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$170 Roundtrip, found 6 days ago
$170
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, May 27 from Newark Liberty Intl. Airport to Greater Rockford, returning Fri, May 29, priced at $170 found 6 days ago
Mon, May 25 - Wed, May 27
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago
Select United flight, departing Mon, May 25 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, May 27, priced at $177 found 3 days ago
Thu, May 28 - Tue, Jun 2
DAL
Love Field
MDW
Midway Intl.
$178 Roundtrip, found 6 days ago
$178
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, May 28 from Love Field to Midway Intl., returning Tue, Jun 2, priced at $178 found 6 days ago

Highland Flight Information

Traveling To
Highland
Destination Airport IATA Code
RFD
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, American Airlines, United, Southwest Airlines
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.
Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

May 18 - May 20

2 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $494, price is now $337 per person
$337
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

May 18 - May 20

2 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $604, price is now $368 per person
$368
per person
found 1 day ago
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

May 18 - May 20

2 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $461, price is now $347 per person
$347
per person
found 1 day ago
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See all available trips from Atlanta to Highland
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Highland first class 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

9.4/10 Exceptional! (3,495 reviews)

May 13 - May 15

2 night stay

Atlanta (ATL) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Atlanta (ATL)

United • FirstClass
Price was $865, price is now $693 per person
$693
per person
found 24 hours ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (2,076 reviews)

May 13 - May 15

2 night stay

Atlanta (ATL) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Atlanta (ATL)

United • FirstClass
Price was $958, price is now $786 per person
$786
per person
found 24 hours ago
The room was great the service was good

Reviewed on Feb 16, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,852 reviews)

May 13 - May 15

2 night stay

Atlanta (ATL) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Atlanta (ATL)

United • FirstClass
Price was $1,288, price is now $1,086 per person
$1,086
per person
found 24 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

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Highland

Traveling to Highland and need a cheap flight? Orbitz has great deals on flights to Highland right now. Plus, we offer big discounts on hotel rooms and car rentals for a great money-saving trip.

Find Low Cost Flights to Highland Quickly and Hassle-Free

There are many Internet sites that promise cheap Highland flights, but a busy, bargain-minded trip planner needs more than just budget air tickets. Not only does Orbitz offer the best deals for domestic and international air fare, but we also provide the resources and tools to help you plan your flights to Highland, book your lodging, and look up key attractions in Highland. Our easy search tools and guaranteed low prices let you budget your time and your money so you have more of both to spend on your vacation.

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You no longer need to be sitting at your computer to find amazing Orbitz sales for flights to Highland now we offer cutting-edge mobile tools for many Android and iOS gadgets. These free apps allow you to run a search for discount air fare, look for special vacation packages, or check on your booked Highland flights from any location. Some special deals are only available for mobile customers, so be sure to take advantage of these free downloads today.

Orbitz Customers Are Truly #1

Orbitz takes pride in providing the best customer experience possible, and that effort doesn't end with discount flights to Highland or user-friendly mobile apps and web tools. Orbitz Customer Service is always ready to answer questions and help you with booking, planning, or canceling your Highland flights. When you need us, we’re here for you!

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 $178 for a round-trip flight to Highland. Tickets one-way originating from New York (EWR) 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.