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$108+ Cheap flights from Oakland (OAK) to Midway (MDW)

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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MDW
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Oakland to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Midway (MDW). 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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

September

Cheapest in

March

Round-trip from

$237
(Southwest)

One-way from

$108
(Southwest)
Provider with most accurate pricing for Oakland-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Oakland-Chicago Midway flights.
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High demand for flights, 26% potential price rise
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Best time to find cheap flights, 33% potential price drop
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From Oakland to Chicago Midway
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One-way flight from Oakland to Chicago Midway
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Find flight deals from Oakland to Midway

Cheapest flights from Oakland to Midway
Explore the most affordable flight options available from Oakland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2024.

This Southwest deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/254:25 pmOAK - MDW
1 stop5h 50mSouthwest
Wed 1/89:40 amMDW - OAK
Nonstop4h 55mSouthwest
Deal found 11/19$267
This Delta deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/255:30 amOAK - MDW
2 stops9h 41mDelta
Wed 1/82:08 pmMDW - OAK
2 stops11h 48mDelta
Deal found 11/19$304
This Mytrip deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/245:16 pmOAK - MDW
2 stops19h 08mMultiple Airlines
Tue 11/2612:31 pmMDW - OAK
2 stops12h 26mMultiple Airlines
Deal found 11/20$697
This Mytrip deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/45:59 pmOAK - MDW
1 stop12h 46mVolaris
Fri 12/67:55 pmMDW - OAK
2 stops20h 30mVolaris
Deal found 11/20$841

Find flights from Oakland to Midway within your budget

Customize your flight search to find flights from Oakland to Midway 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 2,629,791 searches. Data last updated November 20, 2024.

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Any airport

Fly to

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Route

Depart

Return

Price

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 2/22

3:20 pm-11:10 pm

1 stop5h 50m

Chicago Midway

Sat 3/1

5:10 pm-8:00 pm

Nonstop4h 50m

$237

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 1/7

5:35 am-5:47 pm

2 stops10h 12m

Chicago Midway

Fri 1/10

10:57 am-11:56 pm

2 stops14h 59m

$286

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 1/13

6:32 am-12:13 am

2 stops15h 41m

Chicago Midway

Sun 1/19

7:15 am-10:39 pm

2 stops17h 24m

$404

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Mon 3/17

11:59 pm-7:14 pm

1 stop17h 15m

Chicago Midway

Wed 3/19

8:39 pm-3:25 pm

2 stops20h 46m

$623

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Sat 2/22

3:20 pm-11:10 pm

1 stop5h 50m

$108

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Wed 1/15

5:35 am-5:47 pm

2 stops10h 12m

$133

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Tue 3/18

4:55 pm-7:14 pm

3 stops24h 19m

$285

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Thu 3/27

4:55 pm-7:14 pm

2 stops24h 19m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Compare providers for flights from Oakland to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oakland to Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Oakland, California-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oakland, California-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Oakland to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Oakland 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.

Travel insights for flights from Oakland to Midway

Get recent, data-driven insights about flights from Oakland to Midway including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Oakland, California to Chicago Midway Airport?

Currently, December is the cheapest month in which you can book a flight from Oakland, California to Chicago Midway Airport (average of $159). Flying from Oakland, California to Chicago Midway Airport in July is currently the most expensive (average of $231). 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.

What is the cheapest time of day to fly from OAK to MDW?

Find hourly flight availability from Oakland to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 20, 2024.

When flying from Oakland, California to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 5% versus a flight at noon.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated November 20, 2024.
Read reviews from past customers who have flown Southwest and Delta from Oakland to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

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
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

Reviews

1 / 10

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

Volaris
6.7
Okay
1,287 reviews
Southwest
8.1
Very good
5,014 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Food

7.2

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 Oakland to Midway. 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 Oakland to Chicago Midway?

    Located just 7.0 mi from the city center, Oakland is the airport most travelers will use when flying to Chicago Midway from Oakland. Booking flights from Oakland (OAK) to Chicago Midway should be relatively easy as there is 1 daily outbound flight to Chicago Midway from 2 different airlines.

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

    Southwest, at $237, was found to be the cheapest airline from Oakland, California to Chicago Midway Airport.Alternate airlines to your destination round-trip include Delta and Volaris. Southwest is 35% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Oakland, California to Chicago Midway Airport one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $108. Users have also found prices from $133 and $285 on Delta and Volaris, respectively.

  • What are the cheapest flights from Oakland, California to Chicago Midway Airport?

    Looking for the cheapest flight from Oakland, California to Chicago Midway Airport? While on average our users pay $368, our data indicates the cheapest price to be $202. The most popular route (Oakland - Chicago Midway), is priced around $258.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Oakland, California to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from Oakland, California to Chicago Midway Airport (average of $159). Flying from Oakland, California to Chicago Midway Airport in July is currently the most expensive (average of $231). 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.

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Alternative routes for Oakland to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Oakland to Midway

Discover the top 2 airlines that operate flights from Oakland to Midway. 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$242FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$262Average$390FlexibilityNo cancel feeOn-time63%
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