CHI - EYW

$84 Find Cheap Flights from Chicago to Key West

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Key West departing on 4/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Key West

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$293
Overall average: $549
Multiple Airlines
Sun 3/8Fri 3/13
ORD - EYW • 1 stop
Cheapest non-stop
$305
Typical prices: $418-$804
United Airlines
Sat 3/14Mon 3/16
ORD - EYW • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers extra legroom for comfort.
EYW is a ten-minute drive to Old Town Key West.
Expert advice
Expert advice
Expert advice
Expert advice
Video guide: How to find cheap flights to Key West
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Top airlines
American Airlines
Cheapest • from $296 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD
-
EYW
Cheapest
ORD
-
EYW
Most popular
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 12% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Key West!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Chicago to Key West (CHI-EYW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Key West that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Key West

Sun, Mar 8 - Fri, Mar 13
Multiple Airlines Logo
8:05 am - 12:26 pm
ORD
-
EYW
27h 21m
1 stop
Multiple Airlines Logo
2:35 pm - 10:01 pm
EYW
-
ORD
32h 26m
2 stops
$293Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
8:16 pm - 12:21 pm
ORD
-
EYW
15h 05m
2 stops
Multiple Airlines Logo
1:06 pm - 7:47 pm
EYW
-
ORD
7h 41m
1 stop
$294Multiple Airlines
Tue, Mar 17 - Sun, Mar 22
Multiple Airlines Logo
6:36 pm - 11:30 am
ORD
-
EYW
15h 54m
1 stop
Multiple Airlines Logo
12:25 pm - 7:51 pm
EYW
-
ORD
8h 26m
1 stop
$295Multiple Airlines
Sat, Apr 4 - Thu, Apr 9
American Airlines Logo
3:16 pm - 10:37 pm
ORD
-
EYW
6h 21m
1 stop
American Airlines Logo
6:46 pm - 9:35 pm
EYW
-
ORD
3h 49mnonstop
$296American Airlines
Sun, Feb 22 - Fri, Feb 27
Multiple Airlines Logo
3:40 pm - 12:26 pm
ORD
-
EYW
19h 46m
2 stops
Multiple Airlines Logo
9:49 am - 5:03 pm
EYW
-
ORD
8h 14m
1 stop
$297Multiple Airlines
Tue, Mar 3 - Sat, Mar 7
Delta Logo
10:49 am - 5:01 pm
MDW
-
EYW
5h 12m
1 stop
Delta Logo
5:56 pm - 10:31 pm
EYW
-
MDW
5h 35m
1 stop
$298Delta
Tue, Mar 3 - Mon, Mar 9
Delta Logo
11:18 am - 5:01 pm
ORD
-
EYW
4h 43m
1 stop
Delta Logo
6:25 pm - 11:54 pm
EYW
-
ORD
6h 29m
1 stop
$298Delta
Sat, Feb 21 - Mon, Feb 23
Multiple Airlines Logo
12:44 pm - 9:06 am
ORD
-
EYW
19h 22m
1 stop
Multiple Airlines Logo
9:49 am - 10:51 am
EYW
-
ORD
26h 02m
2 stops
$299Multiple Airlines
Sat, Apr 4 - Thu, Apr 9
Spirit Airlines Logo
12:45 pm - 11:30 am
ORD
-
EYW
21h 45m
3 stops
Spirit Airlines Logo
12:25 pm - 7:51 pm
EYW
-
ORD
8h 26m
1 stop
$300Spirit Airlines
Sat, Mar 14 - Thu, Mar 19
Spirit Airlines Logo
6:10 pm - 11:30 am
ORD
-
EYW
16h 20m
1 stop
Spirit Airlines Logo
12:25 pm - 11:17 pm
EYW
-
ORD
11h 52m
1 stop
$302Spirit Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Key West flights

Get data-powered insights and trends into flights from Chicago to Key West to help you find the cheapest flights, the best time to fly and much more.

Find cheap flights to Key West
Find cheap flights to Key West

Planning a trip from Chicago to Key West? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

How much is a round-trip flight from Chicago to Key West?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Key West departing in March.

What is the cheapest Chicago to Key West flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Key West costs $249 on the route between Chicago O'Hare Intl Airport (ORD) and Key West (EYW). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Key West?

The average price of all round-trip flights from Chicago to Key West clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Key West, look for departures on Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Key West, Wednesday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Chicago to Key West?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Key West, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Key West is January, where tickets cost $385 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $492 and $483 respectively.

Can I save money by flying with a layover from Chicago to Key West?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $442 on average.

How far in advance should I book a flight from Chicago to Key West?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Key West, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Key West, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Key West

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Paul Rubio

Paul Rubio

Expert on EYW

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

Good to know

Low seasonSeptember
Cheapest flight$84
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Chicago O'Hare Airport to Key West

When to book flights from Chicago to Key West

Are your dates flexible? Find out the best times to travel from Chicago to Key West based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Key West

  • Does Key West Airport (EYW) have pet relief areas?

    Key West Airport has pet relief areas located at arrivals and departures. The designated relief areas in arrivals are outside the baggage claim, near the blue curbside for passenger pick-ups while those in departures are near the restrooms. You’ll find waste bags and trash containers which visitors can use to clean after their pets.

  • Where can I get a rental car at Key West Airport?

    Renting a car is sometimes more convenient than taking a taxi. Some rental car companies at Key Stone Airport are Hertz, Avis, Budget, and Dollar. Once you land at the airport and are looking to rent a car, head to the car rental counters in the arrivals baggage claim area.

  • Does Chicago Midway have a USO Military Lounge?

    USO military lounges provide a space for military personnel and their family members to sit, relax and wait for their flight. Chicago Midway Airport has a USO military lounge located at concourse C post-security. The lounge features free internet, complimentary food and beverages, reading materials, and a TV for entertainment.

  • Does Chicago O'Hare airport have social services agency?

    Chicago O'Hare has unique services for passengers who need guidance, support, and advocacy. Travelers Aid Chicago social service in terminal 2 of O'Hare Airport provides social assistance for travelers and visitors and crisis intervention information.

  • What is the cheapest flight from Chicago to Key West?

    In the last 3 days, the lowest price for a flight from Chicago to Key West was $84 for a one-way ticket and $293 for a round-trip.

  • Do I need a passport to fly between Chicago and Key West?

    A passport is not required to fly from Chicago to Key West.

  • Which airports will I be using when flying from Chicago to Key West?

    Chicago is served by 2 major airports and there is only 1 main airport in Key West. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at Key West.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Key West?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Key West flight route.

  • Which aircraft models fly most regularly from Chicago to Key West?

    The Embraer 170 is the aircraft model that flies most regularly on the Chicago to Key West flight route.

  • Which airline alliances offer flights from Chicago to Key West?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Key West, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Key West?

    There are nonstop flights from Chicago to Key West on a daily basis.

  • Which is the best airline for flights from Chicago to Key West, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Key West are Delta and United Airlines. With an average price for the route of $413 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $449 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Key West?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Key West.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Key West?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Key West from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Key West?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Key West with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Key West?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Key West from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Key West

  • Looking for a cheap flight? 25% of our users found flights on this route for $158 or less one-way and $327 or less round-trip.
  • You might be flying from Chicago to Key West through Chicago Midway Airport (MDW). If this is the case and you have some time to kill at the airport, you can browse through the airport's art. Chicago Midway has art displays located at Concourse A.
  • Airports can get busy, causing passengers to feel overwhelmed. One of the unique things about Chicago Midway Airport is the yoga room. The room in concourse C provides a quiet and calming space for passengers to meditate and take a timeout while waiting for their flight.
  • You may be flying to Key West from Chicago O'Hare airport (ORD). If you're traveling with your family, you should wait for your flight at the family lounge. The lounge is in Terminal 2, just beyond security. It has a play area for kids, device charging stations, stroller parking spaces for those traveling with infants, and live entertainment at various times throughout the year, featuring musicians, caricature artists, and more.
  • Chicago O'Hare Airport is unique for a health club facility. If you're looking for a place to exercise before a flight, consider becoming a member of the Hilton athletic club. Members enjoy access to facilities like a sauna, steam room, lap pool, and locker rooms for a small fee. The health club is inside the Hilton Chicago O'Hare Airport Hotel, directly across the domestic terminals 1, 2, and 3.
  • Getting to the center or downtown Key West from the airport is easier with the availability of buses. The Keys West Transit and the Lower Keys shuttle serve the airport, with buses available every 30min. The bus service is at Faraldo Circle outside the Airport exit.

Prefer to fly direct from Chicago to Key West?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Key West.
Find which airlines fly direct from Chicago to Key West Airport, which days they fly and book direct flights.

Direct departures

Chicago to Key West

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Key West to Chicago

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Reviews of the top 4 airlines serving from Chicago to Key West

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Key West. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Key West? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8180 reviews
7.2Food
8.5Crew
7.9Comfort
8.1Boarding
7.8Entertainment
Airline reviews

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

2.0 MediocreMichael, Feb 2026
ORD - LGA
Read more Delta reviews

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

The flight was an hour and a half late departing which was inconvenient

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

More comfortable seats, free snacks and soft drinks, some sort of entertainment or WiFi.

Flight has been canceled 10 minutes before the departure time and no explanation was given. What a joke of a company

All of our flights were canceled, though every other airline was flying out and in

Great, but seats are terrible. Way too cramped for any human.

Everything was OK, the deicing took a long time, our connections were almost missed.

Flight was cancelled. But kayak thought it was still on time.

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

You can’t beat Spirit’s prices on tickets, especially with the positive experience that comes with it! I appreciated the timeliness of Spirit airlines. The crew in the airport was very kind and wished you a good flight by name. The crew on the flight was attentive and friendly. Overall, I am very pleased with my experience with Spirit.

This was my best experience with spirit. I flew you guys 4 times and I must say this was the BEST

I didn't have a flight because of a ticking problem that was discovered at the airport at checkin for the initial flight of the round trip.

Everything you need to know for your flight from Chicago to Key West

Information on your arrival and departure airports