Cheap flights To Highland (RFD) from $48

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Cheap Flights to Highland from $48 One Way, $92 Round Trip

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

Fri, Jan 22 - Wed, Feb 3
AZA
Phoenix - Mesa Gateway
RFD
Greater Rockford
$92 Roundtrip, found 15 hours ago
$92
Roundtrip
found 15 hours ago
Select Allegiant Air flight, departing Fri, Jan 22 from Phoenix - Mesa Gateway to Greater Rockford, returning Wed, Feb 3, priced at $92 found 15 hours ago
Thu, Jan 14 - Mon, Jan 18
SFB
Orlando Sanford Intl.
RFD
Greater Rockford
$97 Roundtrip, found 6 days ago
$97
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Thu, Jan 14 from Orlando Sanford Intl. to Greater Rockford, returning Mon, Jan 18, priced at $97 found 6 days ago
Thu, Feb 4 - Sun, Feb 7
SFB
Orlando Sanford Intl.
RFD
Greater Rockford
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Feb 4 from Orlando Sanford Intl. to Greater Rockford, returning Sun, Feb 7, priced at $97 found 1 day ago
Sun, Jan 31 - Sun, Feb 7
SFB
Orlando Sanford Intl.
RFD
Greater Rockford
$99 Roundtrip, found 13 hours ago
$99
Roundtrip
found 13 hours ago
Select Allegiant Air flight, departing Sun, Jan 31 from Orlando Sanford Intl. to Greater Rockford, returning Sun, Feb 7, priced at $99 found 13 hours ago
Thu, Jan 21 - Mon, Jan 25
SFB
Orlando Sanford Intl.
RFD
Greater Rockford
$104 Roundtrip, found 4 days ago
$104
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Thu, Jan 21 from Orlando Sanford Intl. to Greater Rockford, returning Mon, Jan 25, priced at $104 found 4 days ago
Mon, Jan 25 - Wed, Feb 3
AZA
Phoenix - Mesa Gateway
RFD
Greater Rockford
$106 Roundtrip, found 4 days ago
$106
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Mon, Jan 25 from Phoenix - Mesa Gateway to Greater Rockford, returning Wed, Feb 3, priced at $106 found 4 days ago
Thu, Feb 4 - Sun, Feb 7
SFB
Orlando Sanford Intl.
RFD
Greater Rockford
$108 Roundtrip, found 3 days ago
$108
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Feb 4 from Orlando Sanford Intl. to Greater Rockford, returning Sun, Feb 7, priced at $108 found 3 days ago
Thu, Feb 4 - Sun, Feb 7
SFB
Orlando Sanford Intl.
RFD
Greater Rockford
$111 Roundtrip, found 3 days ago
$111
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Feb 4 from Orlando Sanford Intl. to Greater Rockford, returning Sun, Feb 7, priced at $111 found 3 days ago
Thu, Jan 14 - Mon, Jan 18
SFB
Orlando Sanford Intl.
RFD
Greater Rockford
$112 Roundtrip, found 3 days ago
$112
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Jan 14 from Orlando Sanford Intl. to Greater Rockford, returning Mon, Jan 18, priced at $112 found 3 days ago
Thu, Jan 28 - Sun, Jan 31
LAS
Harry Reid Intl.
RFD
Greater Rockford
$113 Roundtrip, found 2 days ago
$113
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Jan 28 from Harry Reid Intl. to Greater Rockford, returning Sun, Jan 31, priced at $113 found 2 days ago

Highland Flight Information

Traveling To
Highland
Destination Airport IATA Code
RFD
Number of Airlines Serving
Airlines
Allegiant Air
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 Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Dec 20 - Dec 23

3 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Price was $562, price is now $421 per person
$421
per person
found 1 day ago
Sheraton Grand Chicago Riverwalk
4.0-star property

Sheraton Grand Chicago Riverwalk

Dec 20 - Dec 23

3 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $649, price is now $457 per person
$457
per person
found 1 day ago
Stay One Chicago
4.0-star property

Stay One Chicago

Dec 31 - Jan 4

4 night stay

Fort Lauderdale (FLL) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Fort Lauderdale (FLL)

Frontier Airlines • Coach
Price was $1,272, price is now $961 per person
$961
per person
found 4 hours ago
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Highland first class flight packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express South Haven by IHG
2.5-star property

Holiday Inn Express South Haven by IHG

9.4/10 Exceptional! (644 reviews)

Dec 23 - Dec 27

4 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • FirstClass

Chicago (ORD) to Atlanta (ATL)

American Airlines • FirstClass
Price was $1,493, price is now $1,489 per person
$1,489
per person
found 1 day ago

Glenn Meadow Bed and Breakfast
4.0-star property

Glenn Meadow Bed and Breakfast

9.8/10 Exceptional! (153 reviews)

Dec 23 - Dec 27

4 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • FirstClass

Chicago (ORD) to Atlanta (ATL)

American Airlines • FirstClass
Price was $1,630, price is now $1,572 per person
$1,572
per person
found 1 day ago
We only stayed one night but I wish we could have stayed longer. The B&B was very clean, comfortable and modern. Our hosts, Tracy and Mark were so much fun to talk to and the breakfast was fantastic. The location was very peaceful and not too far from South Haven which is a fantastic place to visit.

Reviewed on Nov 5, 2026

Historic Hotel Nichols
2.0-star property

Historic Hotel Nichols

9.6/10 Exceptional! (224 reviews)

Dec 23 - Dec 27

4 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • FirstClass

Chicago (ORD) to Atlanta (ATL)

American Airlines • FirstClass
Price was $1,697, price is now $1,652 per person
$1,652
per person
found 1 day ago
Clean room

Reviewed on Nov 9, 2026

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Highland

End your search for discount fares on flights to Highland. Orbitz has all the best prices on Highland flights. With Orbitz, you can expect:

Cheap Deals on Flights to Highland

We offer big discounts and last-minute savings on Highland flights. We make it easy for you to research, plan, and book your flight to Highland — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.

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Get alerts, updates, or book your Highland flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your Highland flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your Highland flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.

Great Customer Care

We want to make your travel booking experience smooth and easy, from planning and researching Highland flights to the actual booking. If you want to cancel your flight to Highland, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.

Miles or Points Toward Frequent Flyer Programs

Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to Highland with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.

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 $113 for a round-trip flight to Highland. Tickets one-way originating from Orlando (SFB) dropped to just $48 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.