Cheap flights from Oakland to Chicago Midway (OAK - MDW)

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How to find the cheapest flight from
Oakland (OAK) to Chicago Midway (MDW)

OAK - MDW
Price
$89 - $446
MDW
Temperature
33.8 - 84.2 °F
MDW
Rainfall
0.7 - 4.3 inches

Popular in

October

High demand for flights, 27% potential price rise

Cheapest in

August

Best time to find cheap flights, 73% potential price drop

Average price

$303

Average for round-trip flights in April 2021

Round-trip from

$89

From Oakland to Chicago Midway

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
How far in advance should I book a flight from Oakland to Chicago Midway?

Travelers have found it’s best to book a flight 20 days in advance to save up to 10% 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 20 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 Oakland to Chicago Midway 1-2 weeks in advance for as low as $137, or $157 for flights within the next 24 hours.

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

April can be a great time to fly to Chicago Midway from Oakland with a flight ticket averaging about $135. Cheapflights users have found deals in the month of April for as cheap as $33. The most expensive prices can be found in the month of December.

Cheap flights from Oakland to Chicago Midway in April, May 2021

14 May - 18 May
$225pp
OAK
Oakland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
OAK
Oakland
8 May - 11 May
$249pp
OAK
Oakland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
OAK
Oakland
15 May - 20 May
$304pp
OAK
Oakland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
OAK
Oakland

Oakland to Chicago Midway 2021 flight deals

14 May - 18 May
$225pp
OAK
Oakland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
OAK
Oakland
8 May - 11 May
$249pp
OAK
Oakland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
OAK
Oakland
3 Jun - 8 Jun
$254pp
OAK
Oakland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
OAK
Oakland

Last minute flights from Oakland to Chicago Midway

22 Apr - 4 May
$391pp
OAK
Oakland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
OAK
Oakland
22 Apr - 2 May
$470pp
OAK
Oakland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
OAK
Oakland
21 Apr - 30 Apr
$492pp
OAK
Oakland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
OAK
Oakland

One-way flights to Chicago Midway from Oakland

6:05 am - 7:48 pm
Delta
2 Stops
11h 43m
OAK - MDW
Delta
$249
Delta
4:47 am - 3:36 am
Allegiant Air
3 Stops
44h 49m
OAK - MDW
Allegiant Air
$257
Kiwi.com
9:09 am - 11:24 am
Multiple Airlines
3 Stops
24h 15m
OAK - MDW
Multiple Airlines
$259
Kiwi.com

Related info for your journey

Flight FAQs

From Oakland to Chicago Midway

Are flight prices decreasing from Oakland to Chicago Midway due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Oakland and Chicago Midway for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Oakland to Chicago Midway to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. Alaska Airlines and Delta are some airlines that have done so. Some of the new policies that have been implemented to accommodate travelers flying from Oakland to Chicago Midway are improved sanitation, HEPA filters, mask requirements, social distance seating (for a limited time), and pre-flight testing for antibodies and symptoms. Policies will vary by airline.

Which airlines flying from Oakland to Chicago Midway have flexible cancellations due to COVID-19?

Some of our airline partners flying from Oakland to Chicago Midway have new flexible policies in place due to COVID-19. United Airlines, Delta, and Spirit Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like United Airlines with this kind of flexibility.

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

Yes, there are multiple flights from Oakland to Chicago Midway for under $300. The cheapest flight booked recently is on Delta for just $225, but on average you can expect to pay $314.

Are there nonstop flights from Oakland to Chicago Midway for under $200 on Cheapflights?

There are no nonstop flights from Oakland to Chicago Midway, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Oakland to Chicago Midway for under $400?

There are currently 20+ open flights from Oakland to Chicago Midway within the next 7 days for less than $400.

Does it rain more in Oakland or Chicago Midway?

When traveling, we recommend packing in preparation to handle common weather conditions. The rainfall in Oakland is typically less than Chicago Midway. We can gather that this will continue over the next 9 days.

Is Oakland weather warmer or cooler than Chicago Midway?

Expect the weather to be around 84 °F on average in July. As the temperature peaks, try to get your plans done early, as flight price and availability will have an impact on your travels. The climate in Chicago Midway is generally hotter than in Oakland.

How long is the flight from Oakland to Chicago Midway?

For as low as $361, Delta can have you in Chicago Midway from Oakland in 8h 41m.

What is the cheapest airline to fly from Oakland to Chicago Midway round-trip?

Delta, at $225, was found to be the cheapest airline from Oakland to Chicago Midway.. You may be able to fly from Oakland to Chicago Midway for 30% less than the average price by searching for this airline.

What are the cheapest airlines to fly from Oakland to Chicago Midway one-way?

One-way options have recently been found by users for as low as $113 on Delta. Another option is Allegiant Air, who have fights from $257.

Alternative routes for Oakland to Chicago Midway

Destination information for Chicago Midway

Average temperature for April in Chicago Midway
62.6 °F
Avg rainfall for April in Chicago Midway
2.3 ″

Airports servicing Oakland

Airports servicing Chicago

Top 4 airlines flying from Oakland to Chicago Midway

Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$151 $308 No cancel fee 65%
United Airlines
$268 $425 No cancel fee 69%
American Airlines
$302 $433 No cancel fee 71%
Delta
$300 $637 No cancel fee N/A

Hourly flight availability from Oakland to Chicago Midway

Morning 6 AM to noon 100% of OAK to MDW departures
Early morning Midnight to 6 AM 0% of OAK to MDW departures
Afternoon Noon to 6 PM 0% of OAK to MDW departures
Evening 6 PM to midnight 0% of OAK to MDW departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Oakland to Chicago Midway
Sunday
1 daily flight
Monday
4 daily flights
Tuesday
0 flights
Wednesday
0 flights
Thursday
1 daily flight
Friday
1 daily flight
Saturday
0 flights