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

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The best prices from Oakland to Chicago Midway are usually found in May or February, booked 57 days in advance, depart on a Monday or Wednesday and return on a Wednesday

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

OAK - MDW
Price
$227 - $446
MDW
Temperature
33.8 - 84.2 °F
MDW
Rainfall
0.7 - 4.3 inches
Popular in October High demand for flights, 18% potential price rise
Cheapest in May Best time to find cheap flights, 38% potential price drop
Round-trip from $227 From Oakland to Chicago Midway
One-way from $133 One-way flight 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.
What is the cheapest day to fly round-trip from Oakland to Chicago Midway?

Saturday flights are generally found to be more expensive for flights from Oakland to Chicago Midway. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago Midway.

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

Travelers have found it’s best to book a flight 37 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 37 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 $177, or $177 for flights within the next 24 hours.

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

A simple way to save on the total cost of your ticket is to fly from Oakland to Chicago Midway in the noon. If you’re flexible enough to do this you can expect to save up to 9% on your trip compared to booking a flight in the afternoon.

Cheap flights from Oakland to Chicago Midway in August, September 2020

The best prices found for OAK to MDW flights for August, September
25 Jul - 23 Aug
$279pp
OAK
Oakland
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
OAK
Oakland
28 Jul - 2 Aug
$312pp
OAK
Oakland
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
OAK
Oakland
23 Jul - 26 Jul
$335pp
OAK
Oakland
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
OAK
Oakland

Oakland to Chicago Midway 2020 flight deals

Cheap flights to Chicago Midway from Oakland found for this year
16 Sep - 23 Sep
$218pp
OAK
Oakland
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
OAK
Oakland
25 Jul - 23 Aug
$279pp
OAK
Oakland
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
OAK
Oakland
28 Jul - 2 Aug
$312pp
OAK
Oakland
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
OAK
Oakland

Last minute flights from Oakland to Chicago Midway

Late deals on round-trip flights to Chicago Midway from Oakland, departing today and this week
25 Jul - 23 Aug
$279pp
OAK
Oakland
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
OAK
Oakland
28 Jul - 2 Aug
$312pp
OAK
Oakland
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
     
3 STOPS
OAK
Oakland
23 Jul - 26 Jul
$335pp
OAK
Oakland
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
OAK
Oakland

One-way flights to Chicago Midway from Oakland

The cheapest one-way flights from Oakland to Chicago Midway
6:30 pm - 5:43 am
Delta
1 Stop
9h 13m
OAK - MDW
Delta
$133
Delta
3:59 pm - 2:33 am
Multiple Airlines
3 Stops
32h 34m
OAK - MDW
Multiple Airlines
$228
Kiwi.com
11:26 am - 12:37 pm
Allegiant Air
3 Stops
47h 11m
OAK - MDW
Allegiant Air
$238
Kiwi.com

Related info for your journey

Useful info, stats and facts about Oakland to Chicago Midway flights.

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.

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 $218, but on average you can expect to pay $800.

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 $300?

There are currently 5+ open flights from Oakland to Chicago Midway within the next 7 days for less than $300.

What days are nonstop flights available from Oakland to Chicago Midway?

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

How many flights depart from Oakland to Chicago Midway on average per day?

On average, you can expect to see 2 flights from Oakland to Chicago Midway a day.
Morning (6am - Noon) - 100% of flight departures

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 3 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 $756, Delta can have you in Chicago Midway from Oakland in 9h 11m. There are 1850 mi between Oakland and Chicago Midway. This flight may include one or multiple stops.

What are the cheapest airlines flying from Oakland to Chicago Midway round-trip?

Delta, at $218, was found to be the cheapest airline from Oakland to Chicago Midway. An alternate airline flying to your destination would be Volaris. You may be able to fly from Oakland to Chicago Midway for 40% less than the average price by searching for these airlines.

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 $133 on Delta. Another option is Allegiant Air, who have fights from $238.

Alternative routes for Oakland to Chicago Midway

Destination information for Chicago Midway

Things to know before you go. Useful info for your trip from Oakland to Chicago Midway
Average temperature for August in Chicago Midway
82.4 °F
Avg rainfall for August in Chicago Midway
3.9 ″

Airports servicing Oakland

Airports servicing Chicago

Hourly flight availability from Oakland to Chicago Midway

Morning 6 AM to noon 69% of OAK to MDW departures
Afternoon Noon to 6 PM 31% of OAK to MDW departures
Early morning Midnight to 6 AM 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
7 daily flights
Monday
7 daily flights
Tuesday
0 flights
Wednesday
6 daily flights
Thursday
7 daily flights
Friday
7 daily flights
Saturday
4 daily flights