Cheap flights To Highland (RFD) from $47

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Cheap Flights to Highland from $47 One Way, $90 Round Trip

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

Tue, Oct 28 - Tue, Oct 28
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$90 Roundtrip, found 23 hours ago
$90
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue, Oct 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Oct 28, priced at $90 found 23 hours ago
Tue, Oct 21 - Tue, Oct 21
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 12 hours ago
$90
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Oct 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Oct 21, priced at $90 found 12 hours ago
Thu, Dec 4 - Sun, Dec 7
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Dec 4 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Sun, Dec 7, priced at $100 found 1 day ago
Thu, Dec 4 - Thu, Dec 11
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Dec 4 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, Dec 11, priced at $100 just found
Wed, Oct 15 - Sat, Oct 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$106 Roundtrip, found 1 day ago
$106
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Oct 15 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 25, priced at $106 found 1 day ago
Wed, Oct 29 - Wed, Oct 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select United flight, departing Wed, Oct 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 29, priced at $134 found 1 day ago
Sat, Feb 7 - Sat, Feb 7
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$134 Roundtrip, found 22 hours ago
$134
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, Feb 7 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sat, Feb 7, priced at $134 found 22 hours ago
Sat, Dec 6 - Tue, Dec 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 9, priced at $137 found 3 days ago
Sat, Nov 15 - Tue, Nov 18
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$141 Roundtrip, found 1 day ago
$141
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Nov 15 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Tue, Nov 18, priced at $141 found 1 day ago
Thu, Dec 18 - Sat, Jan 10
GRR
Gerald R. Ford Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 4 days ago
$154
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Dec 18 from Gerald R. Ford Intl. to O'Hare Intl., returning Sat, Jan 10, priced at $154 found 4 days ago

Highland Flight Information

Traveling To
Highland
Destination Airport IATA Code
RFD
Number of Airlines Serving
Airlines
Frontier Airlines, American Airlines, Spirit Airlines, Southwest Airlines, United
Flight Price
$90
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.
The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

Oct 31 - Nov 5

5 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $902, price is now $504 per person
$504
per person
found 1 day ago
Level Chicago - River North
4.0-star property

Level Chicago - River North

Oct 31 - Nov 5

5 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,215, price is now $676 per person
$676
per person
found 1 day ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Oct 31 - Nov 5

5 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,045, price is now $594 per person
$594
per person
found 1 day ago
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Highland premium 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

9.4/10 Exceptional! (2,427 reviews)

Nov 7 - Nov 11

4 night stay

Miami (MIA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,110, price is now $766 per person
$766
per person
found 1 day ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,716 reviews)

Nov 7 - Nov 11

4 night stay

Miami (MIA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,803, price is now $1,273 per person
$1,273
per person
found 1 day ago
Every employee makes every guest feel like a rockstar. Commitment to quality and guest experience is evident.

Reviewed on Sep 14, 2025

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (2,765 reviews)

Nov 7 - Nov 11

4 night stay

Miami (MIA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,069, price is now $772 per person
$772
per person
found 1 day ago
All around a great location with incredible views. We stayed in a king suite on the 30th floor with views of both the city and lake thanks to architect that designed the building as a triangle that overlooks the Chicago river.

Reviewed on Sep 3, 2025

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Highland first class flight packages

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

Claridge House

9/10 Wonderful! (1,367 reviews)

Oct 31 - Nov 3

3 night stay

San Francisco (SFO) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,415, price is now $1,289 per person
$1,289
per person
found 4 hours ago
Nice property and large, clean, comfortable room. A bit loud one of the nights but not the hotel’s issue. Staff was super helpful. I’d stay again.

Reviewed on Sep 4, 2025

21c Museum Hotel Chicago
4.0-star property

21c Museum Hotel Chicago

8.8/10 Excellent! (1,626 reviews)

Oct 31 - Nov 3

3 night stay

San Francisco (SFO) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,637, price is now $1,478 per person
$1,478
per person
found 4 hours ago
Front desk staff were very welcoming and kind. Cleaning staff was amazing!

Reviewed on Aug 4, 2025

Silversmith Hotel Chicago Downtown
4.0-star property

Silversmith Hotel Chicago Downtown

9.4/10 Exceptional! (1,980 reviews)

Oct 31 - Nov 3

3 night stay

San Francisco (SFO) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,548, price is now $1,416 per person
$1,416
per person
found 4 hours ago
This was my second time staying at Silversmith. Love the location of the hotel. I wish I remember the name of the woman who checked us in but the whole staff is fantastic. I have had nothing but good experiences when staying here. Will be my go to hotel for Chicago.

Reviewed on Sep 9, 2025

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Highland

Finding cheap flights to Highland is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Highland flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Highland through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Highland—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Highland flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Highland with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

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 $90 and $154 for a round-trip flight to Highland. Tickets one-way originating from Atlanta (ATL) dropped to just $47 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.