Cheap flights from Midway (MDW) to Oakland (OAK) from $118

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/27. 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.
MDW — OAK
Jun 2 — Jun 91

Cheap flight deals from Midway to Oakland

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Oakland (OAK). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 28, 2024.

Round-trip from

$268

One-way from

$118
From Chicago Midway to Oakland
One-way flight from Chicago Midway to Oakland

How far in advance should I book a flight from Chicago Midway Airport to Oakland, California?

Users have found that booking a flight from Chicago Midway Airport to Oakland, California at least 52 days early can save you up to 57% on average compared to booking a flight this week. If booking 52 days before your flight isn’t an option for you, users have found flights from Chicago Midway Airport to Oakland, California for as little as $298 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $449 for flights departing within the next 3 days.

What is the cheapest month to fly from Chicago Midway Airport to Oakland, California?

Our data shows that September tends to be the cheapest month to fly to Oakland, California from Chicago Midway Airport. Users have commonly found prices around $306 for the month, but tickets can be as low as $107. Due to multiple factors, prepare for potentially higher prices in March.

When is the cheapest time to fly from Chicago Midway Airport to Oakland, California (MDW - OAK)?

When flying from Chicago Midway Airport to Oakland, California, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Delta flights from Midway to Oakland

Explore cheap flight options specifically provided by Delta for the route between Midway and Oakland. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,696,634 searches. Data last updated May 28, 2024.
Take a peek at the cheapest Delta flights we've detected traveling from Chicago to Oakland. Be sure to come back soon if the deals available don't appeal to you at this time.
Tue 8/131:24 pmMDW - OAK
2 stops12h 27mDelta
Tue 8/206:00 amOAK - MDW
2 stops10h 38mDelta
Deal found 5/28$246
Tue 7/239:18 amMDW - OAK
2 stops8h 49mDelta
Mon 7/2910:52 pmOAK - MDW
2 stops13h 17mDelta
Deal found 5/28$382
Wed 8/141:24 pmMDW - OAK
2 stops12h 27mDelta
Tue 8/206:00 amOAK - MDW
2 stops10h 38mDelta
Deal found 5/28$387
Tue 7/239:18 amMDW - OAK
2 stops8h 49mDelta
Mon 7/2910:52 pmOAK - MDW
1 stop8h 44mDelta
Deal found 5/28$467
Thu 7/181:24 pmMDW - OAK
2 stops12h 27mDelta
Wed 7/245:00 pmOAK - MDW
2 stops13h 38mDelta
Deal found 5/28$472
Mon 8/193:47 pmMDW - OAK
1 stop7h 54mDelta
Sat 8/2410:52 pmOAK - MDW
1 stop8h 34mDelta
Deal found 5/28$551
Mon 8/191:24 pmMDW - OAK
2 stops12h 27mDelta
Sat 8/2410:52 pmOAK - MDW
1 stop8h 34mDelta
Deal found 5/28$556
Mon 8/192:24 pmMDW - OAK
2 stops11h 27mDelta
Sat 8/2410:52 pmOAK - MDW
2 stops11h 50mDelta
Deal found 5/28$561
Wed 7/242:49 pmMDW - OAK
2 stops11h 02mDelta
Mon 7/2910:52 pmOAK - MDW
2 stops13h 17mDelta
Deal found 5/28$571

Cheap Frontier flights from Midway to Oakland

Explore cheap flight options specifically provided by Frontier for the route between Midway and Oakland. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,696,634 searches. Data last updated May 28, 2024.
Some of the lowest-priced Frontier flights we've found at this time heading from Chicago to Oakland. Deals frequently update to provide users with more options.
Thu 10/176:00 amMDW - OAK
2 stops17h 30mFrontier
Sun 10/2011:30 pmOAK - MDW
1 stop11h 21mFrontier
Deal found 5/28$636
Fri 11/228:45 pmMDW - OAK
1 stop21h 14mFrontier
Sun 12/110:30 pmOAK - MDW
2 stops37h 20mFrontier
Deal found 5/27$662
Sat 11/238:45 pmMDW - OAK
1 stop25h 45mFrontier
Sat 11/306:39 pmOAK - MDW
1 stop12h 08mFrontier
Deal found 5/28$667
Tue 8/136:00 amMDW - OAK
2 stops17h 30mFrontier
Tue 8/206:39 pmOAK - MDW
1 stop13h 13mFrontier
Deal found 5/28$676
Sat 11/2310:08 pmMDW - OAK
2 stops24h 22mFrontier
Sat 11/306:39 pmOAK - MDW
1 stop12h 08mFrontier
Deal found 5/28$696
Fri 11/226:05 amMDW - OAK
2 stops16h 25mFrontier
Sun 12/110:30 pmOAK - MDW
2 stops18h 48mFrontier
Deal found 5/27$712
Sat 11/231:24 pmMDW - OAK
2 stops33h 06mFrontier
Sat 11/306:39 pmOAK - MDW
2 stops24h 23mFrontier
Deal found 5/28$731
Thu 6/275:01 amMDW - OAK
2 stops18h 29mFrontier
Thu 7/46:39 pmOAK - MDW
1 stop13h 08mFrontier
Deal found 5/28$733
Fri 6/285:55 amMDW - OAK
2 stops17h 35mFrontier
Mon 7/16:39 pmOAK - MDW
2 stops20h 31mFrontier
Deal found 5/28$838

Cheap Midway to Oakland flights in May & June 2024

Find cheap flight options from Midway to Oakland specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,696,634 searches. Prices were last updated on May 28, 2024.
Check out some of the best flight deals from Chicago to Oakland in 2024. For more flight deals, be sure to check back very soon.
Mon 6/2412:03 pmMDW - OAK
2 stops25h 09mMultiple Airlines
Mon 7/16:15 pmOAK - MDW
3 stops25h 22mMultiple Airlines
Deal found 5/27$575
Mon 6/2412:03 pmMDW - OAK
3 stops26h 17mMultiple Airlines
Mon 7/16:15 pmOAK - MDW
3 stops20h 02mMultiple Airlines
Deal found 5/27$594
Mon 6/2412:03 pmMDW - OAK
2 stops25h 09mMultiple Airlines
Mon 7/111:55 amOAK - MDW
2 stops19h 52mMultiple Airlines
Deal found 5/27$691
Mon 6/2412:03 pmMDW - OAK
2 stops25h 09mMultiple Airlines
Mon 7/16:39 pmOAK - MDW
1 stop13h 08mMultiple Airlines
Deal found 5/27$716
Fri 6/1412:03 pmMDW - OAK
3 stops25h 21mMultiple Airlines
Mon 6/1711:11 amOAK - MDW
3 stops29h 25mMultiple Airlines
Deal found 5/26$730
Fri 6/1412:03 pmMDW - OAK
2 stops25h 21mMultiple Airlines
Mon 6/1711:11 amOAK - MDW
3 stops29h 25mMultiple Airlines
Deal found 5/26$744
Thu 5/303:45 pmMDW - OAK
2 stops10h 06mDelta
Mon 6/35:50 amOAK - MDW
2 stops9h 16mDelta
Deal found 5/27$763
Sat 6/16:00 amMDW - OAK
2 stops12h 07mDelta
Mon 6/35:50 amOAK - MDW
2 stops9h 16mDelta
Deal found 5/28$774
Fri 6/143:45 pmMDW - OAK
1 stop8h 00mDelta
Mon 6/1710:55 pmOAK - MDW
2 stops12h 49mDelta
Deal found 5/26$781

Midway to Oakland 2024 flight deals

Discover exclusive flight deals for travel between Midway and Oakland in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,696,634 searches. Data last updated May 28, 2024.
Check out some of the best flight deals from Chicago to Oakland in 2024. For more flight deals, be sure to check back very soon.
Tue 8/131:24 pmMDW - OAK
2 stops12h 27mDelta
Tue 8/206:00 amOAK - MDW
2 stops10h 38mDelta
Deal found 5/28$246
Thu 11/2811:59 amMDW - OAK
2 stops8h 07mDelta
Fri 12/610:45 pmOAK - MDW
1 stop8h 32mDelta
Deal found 5/27$293
Thu 11/213:45 pmMDW - OAK
1 stop7h 50mDelta
Fri 12/610:45 pmOAK - MDW
1 stop8h 32mDelta
Deal found 5/27$333
Thu 11/2811:59 amMDW - OAK
2 stops8h 07mDelta
Sun 12/1510:45 pmOAK - MDW
1 stop8h 32mDelta
Deal found 5/27$352
Thu 11/2811:59 amMDW - OAK
2 stops8h 07mDelta
Wed 12/46:00 amOAK - MDW
2 stops10h 05mDelta
Deal found 5/27$357
Mon 7/19:35 pmMDW - OAK
Nonstop4h 30mSouthwest
Mon 7/85:10 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 5/27$363
Fri 9/131:05 pmMDW - OAK
1 stop10h 30mDelta
Mon 9/1610:45 pmOAK - MDW
1 stop8h 32mDelta
Deal found 5/27$372
Fri 9/131:05 pmMDW - OAK
1 stop10h 30mDelta
Mon 9/1610:45 pmOAK - MDW
2 stops11h 46mDelta
Deal found 5/27$377
Wed 7/242:49 pmMDW - OAK
2 stops11h 02mDelta
Mon 7/2910:52 pmOAK - MDW
2 stops13h 17mDelta
Deal found 5/28$382

Non-stop flights to Oakland from Midway

Discover non-stop flight options from Midway to Oakland. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,696,634 searches. Data last updated May 28, 2024.
Take a look at some of the direct flights traveling from Chicago to Oakland in the near future. Search for alternative flights from Chicago to Oakland by utilizing the search form above.
Mon 7/19:35 pmMDW - OAK
Nonstop4h 30mSouthwest
Mon 7/85:10 amOAK - MDW
Nonstop4h 05mSouthwest
Deal found 5/27$363

Midway to Oakland flights leaving soon

Find last-minute flight options from Midway to Oakland for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,696,634 searches. Data last updated May 28, 2024.
Consider one of these great deals we found on last-minute flights from Chicago to Oakland. To prevent any unwanted surprises, users should verify their flight info before booking.
Thu 6/62:15 pmMDW - OAK
2 stops11h 38mDelta
Mon 6/1010:55 pmOAK - MDW
1 stop8h 56mDelta
Deal found 5/28$867
Thu 6/62:15 pmMDW - OAK
2 stops11h 38mDelta
Mon 6/1010:55 pmOAK - MDW
2 stops11h 48mDelta
Deal found 5/28$872
Mon 6/32:15 pmMDW - OAK
2 stops11h 36mDelta
Wed 6/55:50 amOAK - MDW
2 stops10h 17mDelta
Deal found 5/28$894
Wed 6/52:15 pmMDW - OAK
2 stops11h 36mDelta
Thu 6/65:50 amOAK - MDW
2 stops9h 16mDelta
Deal found 5/28$1,103

One-way flights to Oakland from Midway

Search for one-way flight options from Midway to Oakland. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,696,634 searches. Data last updated May 28, 2024.
If you're seeking multiple options on one-way flights from Chicago to Oakland, be sure to check out these deals, which are updated often. Those seeking round-trip flights from Chicago to Oakland should utilize the search form at the the top of the page.
Fri 9/271:05 pmMDW - OAK
1 stop10h 30mDelta
Deal found 5/28$118
Thu 7/43:45 pmMDW - OAK
1 stop7h 59mDelta
Deal found 5/28$169
Sun 8/188:13 pmMDW - OAK
2 stops18h 04mMultiple Airlines
Deal found 5/28$175
Sun 9/297:42 pmMDW - OAK
2 stops18h 35mMultiple Airlines
Deal found 5/28$181
Wed 7/109:18 amMDW - OAK
2 stops16h 33mDelta
Deal found 5/28$188
Tue 7/97:19 pmMDW - OAK
2 stops30h 32mDelta
Deal found 5/28$198
Tue 6/183:45 pmMDW - OAK
1 stop8h 00mDelta
Deal found 5/28$203
Sun 8/188:13 pmMDW - OAK
3 stops29h 39mMultiple Airlines
Deal found 5/28$206
Tue 6/42:15 pmMDW - OAK
2 stops11h 36mDelta
Deal found 5/28$208

Find flights from Midway to Oakland within your budget

Customize your flight search to find flights from Midway to Oakland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,696,634 searches. Data last updated May 28, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$246 - $1,215

Route

Depart

Return

Price

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 8/13

2 stops12h 27m

Oakland

Tue 8/20

2 stops10h 38m

$246

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 7/23

2 stops8h 49m

Oakland

Mon 7/29

2 stops13h 17m

$382

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 8/14

2 stops12h 27m

Oakland

Tue 8/20

2 stops10h 38m

$387

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Tue 7/23

2 stops8h 49m

Oakland

Mon 7/29

1 stop8h 44m

$467

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 7/18

2 stops12h 27m

Oakland

Wed 7/24

2 stops13h 38m

$472

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Thu 10/17

2 stops17h 30m

Oakland

Sun 10/20

1 stop11h 21m

$636

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 11/22

1 stop21h 14m

Oakland

Sun 12/1

2 stops37h 20m

$662

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Fri 6/28

2 stops26h 03m

Oakland

Mon 7/1

3 stops20h 02m

$666

Chicago MidwayOakland

MDW - OAK

MDWOAK

Chicago Midway

Wed 6/26

2 stops25h 36m

Oakland

Mon 7/1

1 stop13h 08m

$1,215

Flights are sorted by cheapest first

Deals found on 5/28

No data available for this route at this time. Please check back soon.

Best time to book a flight from Midway to Oakland

Have a flexible travel schedule? Discover the best time to fly to Oakland from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Temperature and rainfall in Oakland by month

Plan your trip to Oakland by taking into account the average temperature and rainfall totals by month.

SFO

Temperature

51.8 - 62.6 °F

Reviews of airlines servicing Oakland

Get insights into the airlines that provide service to Oakland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oakland. Reviews last updated May 28, 2024.
Read through reviews of airlines operating flights from Chicago to Oakland, such as Delta and Frontier. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good
10,476 reviews

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.4

Overall

8.0

Reviews

1 / 10

Crew was nice and courteous. Boarding went smoothly. But we experienced a few minutes of extreme turbulence.

8.0
Very good
10,476 reviews
8.0
Very good
10,476 reviews

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.4

Overall

8.0

Reviews

1 / 10

Crew was nice and courteous. Boarding went smoothly. But we experienced a few minutes of extreme turbulence.

6.6
Okay
1,480 reviews
8.0
Very good
10,476 reviews

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.4

Overall

8.0

Reviews

1 / 10

Crew was nice and courteous. Boarding went smoothly. But we experienced a few minutes of extreme turbulence.

6.3
Okay
4,016 reviews
8.0
Very good
10,476 reviews

Entertainment

8.0

Boarding

8.2

Comfort

7.9

Crew

8.6

Food

7.4

Overall

8.0

Reviews

1 / 10

Crew was nice and courteous. Boarding went smoothly. But we experienced a few minutes of extreme turbulence.

Related info for your journey

Find useful and relevant information for your journey from Midway to Oakland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly into for flights to Oakland from Chicago Midway?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Oakland. 0 airlines have flights to Oakland from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Oakland should not be difficult; the airport handles an average of 2 inbound flights from Chicago Midway per day.

  • Can I find flights from Chicago Midway Airport to Oakland, California for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Oakland, California for under $300. The cheapest flight booked recently is on Delta for just $246, but on average you can expect to pay $575.

  • Are there nonstop flights from Chicago Midway Airport to Oakland, California for under $400 on Cheapflights?

    Cheapflights has at least 1 direct flight from Chicago Midway Airport to Oakland, California under $400. A good price for a nonstop flight from Chicago Midway Airport to Oakland, California is less than $363.

  • Are there last-minute flights available from Chicago Midway Airport to Oakland, California for under $900?

    There are currently 4+ open flights from Chicago Midway Airport to Oakland, California within the next 7 days for less than $900.

  • What days are nonstop flights available from Chicago Midway Airport to Oakland, California?

    Nonstop flights are available for this route on the following days: Saturday.

  • How many flights depart from Chicago Midway Airport to Oakland, California on average per day?

    Travelers can expect 1 flight from Chicago Midway Airport to Oakland, California on average per day.
    Afternoon (Noon - 6pm) - 100% of flight departures

  • How long is the flight from Chicago Midway Airport to Oakland, California?

    A quick flight from Chicago Midway Airport to Oakland, California can take about 12h 27m. Delta provides one of the quickest options available for as low as $246. The distance between Chicago Midway Airport and Oakland, California is about 1850 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago Midway Airport to Oakland, California round-trip?

    Cheapflights users have booked flights from Chicago Midway Airport to Oakland, California round-trip from $246. Another airline that can offer you cheap pricing is Frontier.

  • What does MDW to OAK mean?

    MDW and OAK are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. MDW to OAK refers to a flight route from Chicago Midway Airport to Oakland Airport.

  • Can I find deals for flights from Midway to Oakland that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to Oakland flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to Oakland with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Oakland flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Midway to Oakland that include hotel bookings?

    Yes. In addition to deals on Midway to Oakland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Oakland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Oakland.

  • Can I find deals for business class flights from Midway to Oakland?

    Yes. Cheapflights offers flight deals from Midway to Oakland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Midway to Oakland that allow pets onboard?

    Many airlines flying from Midway to Oakland offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to Oakland?

    Yes, you can often find last-minute deals on Midway to Oakland flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to Oakland, California flight deals updated?

    The Chicago Midway Airport to Oakland, California flight deals you see on this page were last updated on 5/28.

  • When is the best time to book a flight from Chicago Midway Airport to Oakland, California?

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Oakland, California (average of $168). Flying from Chicago Midway Airport to Oakland, California in June is currently the most expensive (average of $237). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Search flights from Midway to Oakland by cabin class

Find flights from Midway to Oakland, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Hourly flight availability from Midway to Oakland

Find hourly flight availability from Midway to Oakland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 28, 2024.
15%of flight departuresEarly morningMidnight to 6 am
19%of flight departuresMorning6 am to noon
52%of flight departuresAfternoonNoon to 6 pm
14%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Midway to Oakland

Explore weekly flight availability from Midway to Oakland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 28, 2024.
Sunday1daily flight
Monday3daily flights
Tuesday2daily flights
Wednesday2daily flights
Thursday3daily flights
Friday3daily flights
Saturday3daily flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Midway to Oakland?

Cheapflights makes it easy to find Midway to Oakland flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Midway to Oakland?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Midway to Oakland for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Midway to Oakland with no change fees?

Need flexible booking options for your flight to Oakland from Midway? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Midway to Oakland become cheaper?

Of course! You can now track prices for flights from Midway to Oakland and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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