Cheap flights To Highland (RFD) from $43

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Cheap Flights to Highland from $43 One Way, $92 Round Trip

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

Sat, Nov 8 - Sat, Nov 8
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$92 Roundtrip, found 10 hours ago
$92
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Sat, Nov 8 from John F. Kennedy Intl. to O'Hare Intl., returning Sat, Nov 8, priced at $92 found 10 hours ago
Tue, Jul 1 - Tue, Jul 1
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$94 Roundtrip, found 3 hours ago
$94
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Tue, Jul 1 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Jul 1, priced at $94 found 3 hours ago
Sat, Nov 8 - Sat, Nov 8
LGA
LaGuardia
ORD
O'Hare Intl.
$97 Roundtrip, found 10 hours ago
$97
Roundtrip
found 10 hours ago
Select United flight, departing Sat, Nov 8 from LaGuardia to O'Hare Intl., returning Sat, Nov 8, priced at $97 found 10 hours ago
Sat, Jul 19 - Sat, Jul 26
LGA
LaGuardia
MDW
Midway Intl.
$99 Roundtrip, found 8 hours ago
$99
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Sat, Jul 19 from LaGuardia to Midway Intl., returning Sat, Jul 26, priced at $99 found 8 hours ago
Wed, Jul 16 - Wed, Jul 23
LGA
LaGuardia
ORD
O'Hare Intl.
$99 Roundtrip, found 11 hours ago
$99
Roundtrip
found 11 hours ago
Select United flight, departing Wed, Jul 16 from LaGuardia to O'Hare Intl., returning Wed, Jul 23, priced at $99 found 11 hours ago
Tue, Jul 8 - Tue, Jul 8
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$100 Roundtrip, found 2 hours ago
$100
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Jul 8, priced at $100 found 2 hours ago
Tue, Jul 1 - Tue, Jul 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 7 hours ago
$102
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Tue, Jul 1 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jul 8, priced at $102 found 7 hours ago
Tue, Jul 1 - Tue, Jul 8
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$107 Roundtrip, just found
$107
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Jul 1 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Jul 8, priced at $107 just found
Tue, Aug 5 - Sat, Aug 9
LGA
LaGuardia
ORD
O'Hare Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 5 from LaGuardia to O'Hare Intl., returning Sat, Aug 9, priced at $107 found 1 day ago
Tue, Aug 5 - Sat, Aug 9
LGA
LaGuardia
ORD
O'Hare Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 5 from LaGuardia to O'Hare Intl., returning Sat, Aug 9, priced at $108 found 1 day ago

Highland Flight Information

Traveling To
Highland
Destination Airport IATA Code
RFD
Number of Airlines Serving
Airlines
Spirit Airlines, JetBlue Airways, Southwest Airlines, United
Flight Price
$92
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.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

Aug 1 - Aug 3

2 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Congress Plaza Hotel
3.5-star property

Congress Plaza Hotel

Jul 19 - Jul 25

6 night stay

Boston (BOS) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Boston (BOS)

United • Coach
Save 100% on your flight
per person
found 1 day ago
The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

Jul 30 - Aug 4

5 night stay

Boston (BOS) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Boston (BOS)

United • Coach
Save 100% on your flight
per person
found 1 day ago
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Highland first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago / Oak Brook
3.0-star property

Hilton Garden Inn Chicago / Oak Brook

8.2/10 Very Good! (1,003 reviews)

Jul 31 - Aug 7

7 night stay

Dallas (DFW) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
I was able to adjust the rm tempt. The room needed a clock. There was only one complenmary tea. Whereas there was three for coffee Overall I liked staying at 1000 Dury Lane as opposed to my usual 10 Dury Lane. Whereas at the Hilton Suite, 10 Dury Lane you cannot adjust the temp. So the room is always cold.

Reviewed on Mar 23, 2025

Four Points by Sheraton Chicago O'Hare Airport
3.0-star property

Four Points by Sheraton Chicago O'Hare Airport

7.6/10 Good! (1,667 reviews)

Jul 31 - Aug 7

7 night stay

Dallas (DFW) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
Shuttle stops running at 11:45 pm. Property showing its age, broken doors, stained carpets, leaking ceiling panels etc

Reviewed on Dec 15, 2024

The Rose Chicago, Tapestry Collection by Hilton
4.0-star property

The Rose Chicago, Tapestry Collection by Hilton

9.4/10 Exceptional! (1,000 reviews)

Jul 31 - Aug 7

7 night stay

Dallas (DFW) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 1 day ago
The receptionist was so nice. I’m happy I chose this hotel. Thank you!

Reviewed on Apr 24, 2025

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Highland

Reach your destination without breaking your budget by booking your flights to Highland using Orbitz. We offer access to all of the best discounts on airfare, travel accommodations and even car rentals. Planning your trip and saving money are easier with Orbitz.

Get Discount Rates On Your Highland Flight

Whether planning ahead or deciding to book your trip at the last minute, Orbitz will provide the lowest rates on Highland flights. Using our free mobile phone apps will make you privy to a number of discounts that are unique to mobile phone users. These are perfect for harried travelers who want to find deals that they can qualify for on the same day.

Make Orbitz Your Official Travel Planner

Orbitz can be used for much more than comparing and booking a discount flight to Highland. We also offer a variety of resources for securing the ideal travel accommodations while staying on budget. Travel tips, hotel reviews, customized suggestions and even detailed images can all be accessed through your mobile phone.

Build A Comprehensive Travel Itinerary

In addition to booking a low cost flight to Highland, you can learn about the best places to visit, the best hotels to stay in and the preferred times for traveling. When you use Orbitz mobile phone apps you can also share your travel itineraries with friends and family members, all with just a few quick taps.

Using Orbitz to secure your Highland flights can save you money and time. Perfect for both the early travel planner and the last minute journey: Orbitz offers phenomenal customer service and unbeatable convenience.

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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 $92 and $108 for a round-trip flight to Highland. Tickets one-way originating from Los Angeles (LAX) dropped to just $43 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.