Cheap flights To Highland (RFD) from $32

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Cheap Flights to Highland from $32 One Way, $63 Round Trip

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

Sun, Jan 11 - Sun, Jan 11
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$63 Roundtrip, found 6 days ago
$63
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Jan 11 from Sky Harbor Intl. to Midway Intl., returning Sun, Jan 11, priced at $63 found 6 days ago
Mon, Jan 19 - Mon, Jan 19
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 16 hours ago
$63
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Mon, Jan 19 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $63 found 16 hours ago
Mon, Dec 8 - Mon, Dec 8
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$64 Roundtrip, found 5 days ago
$64
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Dec 8 from Sky Harbor Intl. to O'Hare Intl., returning Mon, Dec 8, priced at $64 found 5 days ago
Fri, Dec 5 - Mon, Dec 8
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Dec 5 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Dec 8, priced at $68 just found
Thu, Jan 15 - Mon, Jan 19
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jan 15 from Dallas-Fort Worth Intl. to Midway Intl., returning Mon, Jan 19, priced at $68 just found
Tue, Dec 2 - Tue, Dec 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$72 Roundtrip, just found
$72
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Dec 2 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Dec 9, priced at $72 just found
Thu, Nov 27 - Thu, Dec 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$74 Roundtrip, just found
$74
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Nov 27 from Los Angeles Intl. to O'Hare Intl., returning Thu, Dec 4, priced at $74 just found
Wed, Dec 24 - Thu, Jan 1
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 2 hours ago
$88
Roundtrip
found 2 hours ago
Select Sun Country Airlines flight, departing Wed, Dec 24 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Thu, Jan 1, priced at $88 found 2 hours ago
Thu, Jan 22 - Thu, Jan 22
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 4 hours ago
$112
Roundtrip
found 4 hours ago
Select United flight, departing Thu, Jan 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Jan 22, priced at $112 found 4 hours ago
Tue, Jan 20 - Tue, Jan 20
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 20 hours ago
$112
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Tue, Jan 20 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Jan 20, priced at $112 found 20 hours ago

Highland Flight Information

Traveling To
Highland
Destination Airport IATA Code
RFD
Number of Airlines Serving
Airlines
Spirit Airlines, Frontier Airlines, Sun Country Airlines, Southwest Airlines, United, American Airlines
Flight Price
$63
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.
Ameristar Casino Hotel East Chicago
4.0-star property

Ameristar Casino Hotel East Chicago

Dec 12 - Dec 15

3 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $343, price is now $220 per person
$220
per person
found 1 day ago
The Ritz-Carlton, Chicago
5.0-star property

The Ritz-Carlton, Chicago

Dec 21 - Dec 27

6 night stay

Houston (IAH) to Chicago (ORD)

Frontier Airlines • Coach

Chicago (ORD) to Houston (IAH)

Spirit Airlines • Coach
Save 100% on your flight
Price was $1,595, price is now $1,004 per person
$1,004
per person
found 1 day ago
DoubleTree by Hilton Chicago - North Shore Conference Center
4.0-star property

DoubleTree by Hilton Chicago - North Shore Conference Center

Dec 18 - Dec 23

5 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $500, price is now $316 per person
$316
per person
found 17 hours ago
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Highland premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG
3.0-star property

Holiday Inn Chicago O'Hare – Rosemont by IHG

9/10 Wonderful! (2,461 reviews)

Dec 19 - Dec 22

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $647, price is now $565 per person
$565
per person
found 1 day ago
Clean, up to date, great location

Reviewed on Oct 13, 2025

Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.2/10 Very Good! (2,141 reviews)

Dec 19 - Dec 22

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $857, price is now $740 per person
$740
per person
found 1 day ago
Awesome hotel, an island of peace and calm and first class treatment in a sea of chaos at O'Hare airport. Staff, restaurant, services--worth every penny. Early departure? Stay here the night before. We did. Calmly woke up and walked to the terminal thru the underground walkways. Truly pleasant and memorable stay.

Reviewed on Nov 11, 2025

Hyatt Regency O'Hare Chicago
4.0-star property

Hyatt Regency O'Hare Chicago

8.8/10 Excellent! (2,066 reviews)

Dec 19 - Dec 22

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $657, price is now $569 per person
$569
per person
found 1 day ago
The room was great, it was a suite and one of the doors was closed off but one call to the front desk and someone was sent to open it!

Reviewed on Oct 18, 2025

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Highland first class flight packages

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

Hilton Chicago

8.4/10 Very Good! (2,261 reviews)

Dec 18 - Dec 21

3 night stay

Houston (IAH) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $887, price is now $747 per person
$747
per person
found 1 day ago
Nice, clean hotel, friendly staff, very comfortable room, within walking distance from lake Michigan, major attractions, shopping and dining.

Reviewed on Sep 5, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,602 reviews)

Dec 18 - Dec 21

3 night stay

Houston (IAH) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $980, price is now $828 per person
$828
per person
found 1 day ago
One day didn’t receive room service

Reviewed on Sep 2, 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! (2,188 reviews)

Dec 18 - Dec 21

3 night stay

Houston (IAH) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $925, price is now $795 per person
$795
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

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Highland

If you are looking for affordable flights to Highland, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to Highland now available

As you review your budget and travel plans, consider the low fares Orbitz offers on Highland flights. With Orbitz, booking flights to Highland is easy and the lowest prices are guaranteed.

Easy self-help service offered

Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your Highland flights by visiting the Orbitz site or mobile application.

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Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on Highland flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.

Traveler profile updates

After booking your Highland flights, you may access your account profile on the Orbitz site and update your frequent flyer or loyalty membership details. This information will remain on the system and will be available for you to access when you make any future bookings with Orbitz.

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 $63 and $112 for a round-trip flight to Highland. Tickets one-way originating from Dallas (DFW) dropped to just $32 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.