Cheap flights To Highland (RFD) from $42

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Cheap Flights to Highland from $42 One Way, $78 Round Trip

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

Thu, Sep 18 - Thu, Sep 18
PHL
Philadelphia Intl.
MDW
Midway Intl.
$78 Roundtrip, found 6 days ago
$78
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Sep 18 from Philadelphia Intl. to Midway Intl., returning Thu, Sep 18, priced at $78 found 6 days ago
Wed, Aug 27 - Tue, Sep 2
SAN
San Diego Intl.
ORD
O'Hare Intl.
$86 Roundtrip, found 6 hours ago
$86
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Wed, Aug 27 from San Diego Intl. to O'Hare Intl., returning Tue, Sep 2, priced at $86 found 6 hours ago
Sat, Sep 6 - Sat, Sep 6
MCO
Orlando Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 1 hour ago
$87
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Sep 6 from Orlando Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $87 found 1 hour ago
Sat, Aug 2 - Thu, Aug 7
MCO
Orlando Intl.
MDW
Midway Intl.
$92 Roundtrip, found 6 days ago
$92
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Aug 2 from Orlando Intl. to Midway Intl., returning Thu, Aug 7, priced at $92 found 6 days ago
Mon, Sep 15 - Mon, Oct 6
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$95 Roundtrip, found 6 days ago
$95
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Sep 15 from Philadelphia Intl. to O'Hare Intl., returning Mon, Oct 6, priced at $95 found 6 days ago
Tue, Oct 14 - Tue, Oct 14
SAN
San Diego Intl.
ORD
O'Hare Intl.
$133 Roundtrip, found 15 hours ago
$133
Roundtrip
found 15 hours ago
Select Alaska Airlines flight, departing Tue, Oct 14 from San Diego Intl. to O'Hare Intl., returning Tue, Oct 14, priced at $133 found 15 hours ago
Tue, Sep 30 - Tue, Oct 7
SAN
San Diego Intl.
MDW
Midway Intl.
$139 Roundtrip, found 19 hours ago
$139
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Tue, Sep 30 from San Diego Intl. to Midway Intl., returning Tue, Oct 7, priced at $139 found 19 hours ago
Tue, Oct 21 - Sat, Oct 25
SAN
San Diego Intl.
ORD
O'Hare Intl.
$139 Roundtrip, found 23 hours ago
$139
Roundtrip
found 23 hours ago
Select United flight, departing Tue, Oct 21 from San Diego Intl. to O'Hare Intl., returning Sat, Oct 25, priced at $139 found 23 hours ago
Tue, Sep 30 - Tue, Oct 7
SAN
San Diego Intl.
ORD
O'Hare Intl.
$139 Roundtrip, found 19 hours ago
$139
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Tue, Sep 30 from San Diego Intl. to O'Hare Intl., returning Tue, Oct 7, priced at $139 found 19 hours ago
Sat, Sep 20 - Tue, Sep 23
CLD
McClellan-Palomar
ORD
O'Hare Intl.
$161 Roundtrip, found 1 hour ago
$161
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Sep 20 from McClellan-Palomar to O'Hare Intl., returning Tue, Sep 23, priced at $161 found 1 hour ago

Highland ORD Flight Information

Traveling To
Highland
Destination Airport IATA Code
RFD
Number of Airlines Serving
17
Airlines
Frontier Airlines, Spirit Airlines, Alaska Airlines, American Airlines, Southwest Airlines, United
Flight Price
$78
Earliest Departing Flight
AA 2236 6:03AM EDT
Latest Departing Flight
BA 1814 Aug 8 9:15PM EDT

Book Your Flight & Hotel Together & Save

Highland economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Crown Point
2.5-star property

Hampton Inn Crown Point

Sep 25 - Sep 28

3 night stay

Minneapolis (MSP) to Chicago (ORD)

United • Roundtrip • Coach
per person
found 20 hours ago
Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

Sep 19 - Sep 22

3 night stay

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

American Airlines • Coach

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

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Sep 11 - Sep 14

3 night stay

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

United • Coach

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

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Minneapolis to Highland
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Highland premium economy flight packages

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

citizenM Chicago Downtown

9.4/10 Exceptional! (3,315 reviews)

Aug 31 - Sep 2

2 night stay

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

Delta • PremiumEconomy

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

Spirit Airlines • PremiumEconomy
per person
found 15 hours ago
Nice, staff, good location

Reviewed on Jun 22, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,635 reviews)

Aug 31 - Sep 2

2 night stay

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

Delta • PremiumEconomy

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

Spirit Airlines • PremiumEconomy
Save 100% on your flight
per person
found 15 hours ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Pendry Chicago
4.5-star property

Pendry Chicago

9.4/10 Exceptional! (1,006 reviews)

Aug 31 - Sep 2

2 night stay

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

Delta • PremiumEconomy

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

Spirit Airlines • PremiumEconomy
per person
found 15 hours ago
Pendry was historic and great

Reviewed on Jul 5, 2024

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.
Marriott Chicago Schaumburg
3.5-star property

Marriott Chicago Schaumburg

8.8/10 Excellent! (1,005 reviews)

Sep 19 - Sep 22

3 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
The murder 50 feet away was a bit surprising Also the shower door in 934 did not properly close and it looks like it hadn’t in a while thus the water damage on the door

Reviewed on Jul 30, 2025

Hilton Rosemont Chicago O'Hare
3.5-star property

Hilton Rosemont Chicago O'Hare

8.4/10 Very Good! (1,004 reviews)

Sep 19 - Sep 22

3 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
It was very clean and quiet

Reviewed on Mar 27, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG
3.0-star property

Staybridge Suites Chicago O'Hare - Rosemont by IHG

8.8/10 Excellent! (1,000 reviews)

Sep 19 - Sep 22

3 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
Front desk was not helpful with the restaurants that was in the hotel,they were insufficient.

Reviewed on Feb 16, 2025

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

Get the absolute lowest prices on flights to Highland by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

Book Your Flight To Highland Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Highland flights.

Avoid Check-In Hassles When Traveling On Flights to Highland

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Highland flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Highland flight using 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 $78 and $161 for a round-trip flight to Highland. Tickets one-way originating from Philadelphia (PHL) dropped to just $42 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.

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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.