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Cheap flights from San Jose (SJC) to Chicago (CHI) from $88

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 6/26. 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.
SJC — CHI
Jun 11 — Jun 181
From?
To?
Tue 6/11
Tue 6/18
1 adult, Economy
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The best prices from San Jose to Chicago are usually found in October or January, booked 86 days in advance, depart on a Wednesday or Monday and return on a Friday

Cheap flight deals from San Jose to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Chicago (CHI). 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 June 6, 2024.

Popular in

March

Cheapest in

October

Round-trip from

$223

One-way from

$127
High demand for flights, 20% potential price rise
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Best time to find cheap flights, 22% potential price drop
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From San Jose to Chicago (CHI)
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One-way flight from San Jose to Chicago (CHI)
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What is the cheapest day to fly round-trip from San Jose to Chicago?

Travelers have found that booking a Tuesday departure is the best way to save up to 29% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

How far in advance should I book a flight from San Jose to Chicago?

Travelers have found it’s best to book a flight 60 days in advance to save up to 431% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 60 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from San Jose to Chicago 1-2 weeks in advance for as low as $201, or $587 for flights within the next 24 hours.

What is the cheapest month to fly from San Jose to Chicago?

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, October can be a great choice for travel to Chicago. Flights to Chicago from San Jose in October are about $412 on average during October, but can be found for as low as $126.

What is the cheapest time of day to fly from SJC to CHI?

A simple way to save on the total cost of your ticket is to fly from San Jose to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 21% on your trip compared to booking a flight in the morning.

Cheap San Jose to Chicago flights in June & July 2024

Find cheap flight options from San Jose to Chicago specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 6, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Tue 7/26:00 amSJC - ORD
1 stop17h 05mSpirit Airlines
Tue 7/169:49 amORD - SJC
1 stop10h 33mSpirit Airlines
Deal found 6/5$177
Wed 6/263:32 pmSJC - ORD
1 stop12h 17mSpirit Airlines
Tue 7/167:01 amORD - SJC
1 stop11h 59mSpirit Airlines
Deal found 6/5$181
Tue 6/256:00 amSJC - ORD
1 stop17h 05mSpirit Airlines
Mon 8/2611:10 pmORD - SJC
1 stop14h 57mSpirit Airlines
Deal found 6/4$182
Tue 7/96:00 amSJC - ORD
1 stop17h 05mSpirit Airlines
Tue 7/169:49 amORD - SJC
1 stop10h 33mSpirit Airlines
Deal found 6/5$183
Tue 6/253:32 pmSJC - ORD
1 stop7h 33mSpirit Airlines
Mon 8/269:04 pmORD - SJC
2 stops17h 03mSpirit Airlines
Deal found 6/4$187
Tue 6/253:32 pmSJC - ORD
1 stop7h 33mMultiple Airlines
Sun 8/257:30 pmORD - SJC
1 stop23h 21mMultiple Airlines
Deal found 6/4$188
Mon 6/249:12 pmSJC - ORD
1 stop7h 24mSpirit Airlines
Tue 6/2510:01 pmORD - SJC
1 stop12h 23mSpirit Airlines
Deal found 6/5$190
Mon 6/249:12 pmSJC - ORD
1 stop7h 24mMultiple Airlines
Fri 8/236:48 pmORD - SJC
1 stop16h 23mMultiple Airlines
Deal found 6/4$191
Wed 6/263:32 pmSJC - ORD
1 stop12h 17mSpirit Airlines
Mon 7/158:34 pmORD - SJC
1 stop20h 34mSpirit Airlines
Deal found 6/4$193

San Jose to Chicago 2024 flight deals

Discover exclusive flight deals for travel between San Jose and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Tue 8/275:18 pmSJC - ORD
1 stop10h 54mSpirit Airlines
Wed 9/48:37 amORD - SJC
1 stop9h 48mSpirit Airlines
Deal found 6/5$174
Tue 7/26:00 amSJC - ORD
1 stop17h 05mSpirit Airlines
Tue 7/169:49 amORD - SJC
1 stop10h 33mSpirit Airlines
Deal found 6/5$177
Fri 8/2311:30 amSJC - ORD
1 stop11h 33mFrontier
Tue 8/277:30 pmORD - SJC
1 stop23h 21mFrontier
Deal found 6/6$179
Sat 8/1711:31 amSJC - ORD
1 stop10h 40mFrontier
Tue 8/208:00 amORD - SJC
1 stop11h 45mFrontier
Deal found 6/6$180
Wed 6/263:32 pmSJC - ORD
1 stop12h 17mSpirit Airlines
Tue 7/167:01 amORD - SJC
1 stop11h 59mSpirit Airlines
Deal found 6/5$181
Tue 6/256:00 amSJC - ORD
1 stop17h 05mSpirit Airlines
Mon 8/2611:10 pmORD - SJC
1 stop14h 57mSpirit Airlines
Deal found 6/4$182
Tue 7/96:00 amSJC - ORD
1 stop17h 05mSpirit Airlines
Tue 7/169:49 amORD - SJC
1 stop10h 33mSpirit Airlines
Deal found 6/5$183
Tue 6/253:32 pmSJC - ORD
1 stop7h 33mSpirit Airlines
Mon 8/269:04 pmORD - SJC
2 stops17h 03mSpirit Airlines
Deal found 6/4$187
Tue 6/253:32 pmSJC - ORD
1 stop7h 33mMultiple Airlines
Sun 8/257:30 pmORD - SJC
1 stop23h 21mMultiple Airlines
Deal found 6/4$188

San Jose to Chicago flights leaving soon

Find last-minute flight options from San Jose to Chicago 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 3,050,429 searches. Data last updated June 6, 2024.
Have a look at some of the flights available from San Jose to Chicago departing last-minute. Tip: verify your flight details before completing your reservation.
Wed 6/127:00 amSJC - ORD
3 stops21h 00mSpirit Airlines
Tue 6/1810:01 pmORD - SJC
1 stop12h 23mSpirit Airlines
Deal found 6/5$232
Wed 6/127:00 amSJC - ORD
3 stops21h 00mSpirit Airlines
Mon 7/18:26 pmORD - SJC
3 stops29h 33mSpirit Airlines
Deal found 6/4$247
Wed 6/1210:19 amSJC - ORD
1 stop17h 41mSpirit Airlines
Mon 7/18:26 pmORD - SJC
2 stops25h 54mSpirit Airlines
Deal found 6/4$248
Wed 6/126:00 amSJC - RFD
1 stop6h 50mMultiple Airlines
Wed 7/173:40 pmRFD - SJC
1 stop8h 08mMultiple Airlines
Deal found 6/6$254
Wed 6/127:00 amSJC - ORD
3 stops21h 00mSpirit Airlines
Mon 7/112:32 pmORD - SJC
1 stop10h 55mSpirit Airlines
Deal found 6/4$255
Wed 6/1210:19 amSJC - ORD
1 stop17h 41mSpirit Airlines
Mon 7/18:26 pmORD - SJC
1 stop20h 16mSpirit Airlines
Deal found 6/4$256
Wed 6/126:00 amSJC - RFD
1 stop6h 50mMultiple Airlines
Wed 6/193:40 pmRFD - SJC
1 stop6h 41mMultiple Airlines
Deal found 6/6$257
Wed 6/127:00 amSJC - ORD
3 stops21h 00mSpirit Airlines
Tue 6/182:57 pmORD - SJC
2 stops19h 27mSpirit Airlines
Deal found 6/5$258
Wed 6/127:00 amSJC - ORD
3 stops21h 00mSpirit Airlines
Tue 6/189:19 amORD - SJC
3 stops27h 43mSpirit Airlines
Deal found 6/5$280

One-way flights to Chicago from San Jose

Search for one-way flight options from San Jose to Chicago. 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 3,050,429 searches. Data last updated June 6, 2024.
Users traveling one-way from San Jose to Chicago can select one of these great deals. For those needing a return trip from San Jose, there is a search form available above.
Wed 6/263:32 pmSJC - ORD
1 stop12h 17mSpirit Airlines
Deal found 6/6$88
Fri 8/2310:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 6/5$90
Sat 9/2112:58 pmSJC - ORD
1 stop10h 20mSpirit Airlines
Deal found 6/6$93
Tue 6/259:13 pmSJC - ORD
1 stop7h 23mSpirit Airlines
Deal found 6/5$95
Sat 7/136:10 amSJC - RFD
1 stop7h 40mMultiple Airlines
Deal found 6/6$96
Fri 8/2311:30 amSJC - ORD
1 stop11h 33mFrontier
Deal found 6/5$96
Sat 8/3110:20 pmSJC - MDW
1 stop6h 13mFrontier
Deal found 6/5$98
Thu 6/2710:19 amSJC - ORD
1 stop17h 41mSpirit Airlines
Deal found 6/5$99
Sat 8/1711:31 amSJC - ORD
1 stop10h 40mFrontier
Deal found 6/5$100

Find flights from San Jose to Chicago within your budget

Customize your flight search to find flights from San Jose to Chicago 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 3,050,429 searches. Data last updated June 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$180 - $418

Route

Depart

Return

Price

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Thu 9/5

1 stop6h 13m

Chicago Midway

Fri 9/13

1 stop8h 34m

$180

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Fri 9/13

1 stop6h 13m

Chicago Midway

Sun 9/15

1 stop20h 51m

$182

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Tue 8/20

1 stop22h 22m

Chicago Midway

Thu 8/22

1 stop20h 51m

$187

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Mon 7/15

1 stop10h 53m

Chicago O'Hare Intl

Wed 7/17

1 stop11h 03m

$202

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Tue 8/20

1 stop15h 05m

Chicago O'Hare Intl

Thu 8/22

1 stop7h 10m

$208

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Sat 6/22

1 stop7h 23m

Chicago O'Hare Intl

Fri 8/23

1 stop16h 23m

$226

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Tue 9/3

1 stop7h 11m

Chicago O'Hare Intl

Tue 9/10

2 stops9h 52m

$307

San JoseChicago O'Hare Intl

SJC - ORD

SJCORD

San Jose

Mon 9/2

1 stop13h 22m

Chicago O'Hare Intl

Wed 9/11

1 stop10h 41m

$359

San JoseChicago Midway

SJC - MDW

SJCMDW

San Jose

Wed 6/26

1 stop11h 50m

Chicago Midway

Tue 7/2

Nonstop4h 30m

$418

Flights are sorted by cheapest first

Deals found on 6/5

How far ahead should I book a flight from San Jose to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from San Jose to Chicago. Price data was last updated on May 31, 2024.
The best time to book flights from San Jose to Chicago is 86 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Search Deals

What is the cheapest day to fly from San Jose to Chicago?

Use this chart to determine the cheapest time to fly round-trip from San Jose to Chicago. Price data was last updated on June 2, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their San Jose to Chicago flight should consider departing on Sunday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from San Jose to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San Jose 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 Chicago by month

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

CHI

Temperature

23 - 73.4 °F

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 6, 2024.
Get a feel of what it's like to fly with Spirit Airlines, Delta and Alaska Airlines from San Jose to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,918 reviews

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

Food

7.3

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.2
Very good
5,918 reviews
Southwest
8.2
Very good
5,918 reviews

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

Food

7.3

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Alaska Airlines
8.1
Very good
9,222 reviews
Southwest
8.2
Very good
5,918 reviews

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

Food

7.3

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
10,368 reviews
Southwest
8.2
Very good
5,918 reviews

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

Food

7.3

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

United Airlines
7.4
Good
10,696 reviews
Southwest
8.2
Very good
5,918 reviews

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

Food

7.3

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

American Airlines
7.3
Good
14,227 reviews
Southwest
8.2
Very good
5,918 reviews

Crew

8.7

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Overall

8.2

Food

7.3

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Related info for your journey

Find useful and relevant information for your journey from San Jose to Chicago. 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 from for flights from San Jose to Chicago?

    Located just 2.9 mi from the city center, San Jose is the airport most travelers will use when flying to Chicago from San Jose. Booking flights from San Jose (SJC) to Chicago should be relatively easy as there are 6 daily outbound flights to Chicago from 6 different airlines.

  • Can I find flights from San Jose to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from San Jose to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $180, but on average you can expect to pay $206.

  • Are there nonstop flights from San Jose to Chicago for under $400 on Cheapflights?

    Cheapflights has at least 20 direct flights from San Jose to Chicago under $400. A good price for a nonstop flight from San Jose to Chicago is less than $395.

  • Are there last-minute flights available from San Jose to Chicago for under $300?

    There are currently 20+ open flights from San Jose to Chicago within the next 7 days for less than $300.

  • What days are nonstop flights available from San Jose to Chicago?

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

  • How many flights depart from San Jose to Chicago on average per day?

    On average, you can expect to see 2 flights from San Jose to Chicago a day.
    Early Morning (Midnight to 6am) - 50% of flight departures
    Evening (6pm - Midnight) - 50% of flight departures

  • How long is the flight from San Jose to Chicago?

    Airlines like Frontier and Spirit Airlines fly from San Jose to Chicago in about 6h 13m. The time it takes to get you to your destination can typically vary by up to 4h 40m. Airlines will cover a distance of 1835 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from San Jose to Chicago round-trip?

    Cheapflights users have booked flights from San Jose to Chicago round-trip from $180. Another airline that can offer you cheap pricing is Spirit Airlines. You may be able to fly from San Jose to Chicago for 56% less than the average price by searching for these airlines.

  • What are the most popular routes from San Jose to Chicago?

    While some choose either San Jose - Chicago Midway or San Jose - Chicago Greater Rockford, San Jose - Chicago O'Hare Intl is the most popular route from San Jose to Chicago.

  • What are the cheapest flights from San Jose to Chicago?

    Looking for the cheapest flight from San Jose to Chicago? While on average our users pay $932, our data indicates the cheapest price to be $140. The most popular route (San Jose - Chicago O'Hare Intl), is priced around $159.

  • What does SJC to ORD mean?

    San Jose Airport is SJC and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from San Jose to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your San Jose to Chicago 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 San Jose to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter San Jose to Chicago 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 San Jose to Chicago that include hotel bookings?

    Yes. In addition to deals on San Jose to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Chicago?

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

  • Can I find deals for business class flights from San Jose to Chicago?

    Yes. Cheapflights offers flight deals from San Jose to Chicago 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 San Jose to Chicago that allow pets onboard?

    Many airlines flying from San Jose to Chicago 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 San Jose to Chicago?

    Yes, you can often find last-minute deals on San Jose to Chicago 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 San Jose to Chicago flight deals updated?

    The San Jose to Chicago flight deals you see on this page were last updated on 6/6.

  • What are the most popular airlines that fly from San Jose to Chicago?

    Before booking your flight from San Jose to Chicago check out the most popular airlines for this route: American Airlines, Alaska Airlines or Delta.

  • What is the cheapest month to book a flight from San Jose to Chicago?

    Currently, February is the cheapest month in which you can book a flight from San Jose to Chicago (average of $244). Flying from San Jose to Chicago in July is currently the most expensive (average of $324). 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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Alternative routes for San Jose to Chicago
See prices for flight routes from nearby airports that may be better suited for you.

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Top 6 airlines flying from San Jose to Chicago

Discover the top 6 airlines that operate flights from San Jose to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$208FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$100Average$212FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$151Average$269FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$203Average$465FlexibilityNo cancel feeOn-time69%
DeltaCheapest$251Average$500FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$318Average$550FlexibilityNo cancel feeOn-time71%
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Boise to Las Vegas flights
Seattle to Phoenix flights
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Search flights from San Jose to Chicago by cabin class

Find flights from San Jose to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from San Jose to Chicago

Find hourly flight availability from San Jose to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 6, 2024.
67%of flight departuresEarly morningMidnight to 6 am
21%of flight departuresMorning6 am to noon
6%of flight departuresAfternoonNoon to 6 pm
6%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from San Jose to Chicago

Explore weekly flight availability from San Jose to Chicago. 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 June 6, 2024.
Sunday2daily flights
Monday8daily flights
Tuesday7daily flights
Wednesday7daily flights
Thursday8daily flights
Friday8daily flights
Saturday2daily flights

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