Cheap flights from San Diego to Chicago Midway (SAN - MDW)

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How to find the cheapest flight from
San Diego (SAN) to Chicago Midway (MDW)

SAN - MDW
Price
$176 - $514
MDW
Temperature
33.8 - 84.2 °F
MDW
Rainfall
0.7 - 4.3 inches

Popular in

January

High demand for flights, 39% potential price rise

Cheapest in

July

Best time to find cheap flights, 44% potential price drop

Round-trip from

$176

From San Diego to Chicago Midway

One-way from

$109

One-way flight from San Diego 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 San Diego to Chicago Midway?

Users have found that booking a flight from San Diego to Chicago Midway at least 20 days early can save you up to 10% on average compared to booking a flight this week. If booking 20 days before your flight isn’t an option for you, users have found flights from San Diego to Chicago Midway for as little as $137 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 $157 for flights departing within the next 3 days.

What is the cheapest month to fly from San Diego to Chicago Midway?

April can be a great time to fly to Chicago Midway from San Diego 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 San Diego to Chicago Midway in April, May 2021

27 May - 9 Jun
$217pp
SAN
San Diego
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SAN
San Diego
26 May - 2 Jun
$247pp
SAN
San Diego
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SAN
San Diego
27 May - 7 Jun
$250pp
SAN
San Diego
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SAN
San Diego

San Diego to Chicago Midway 2021 flight deals

3 Jun - 5 Jun
$217pp
SAN
San Diego
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SAN
San Diego
2 Jun - 5 Jun
$221pp
SAN
San Diego
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SAN
San Diego
10 Jul - 13 Jul
$242pp
SAN
San Diego
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SAN
San Diego

Last minute flights from San Diego to Chicago Midway

22 Apr - 25 Apr
$308pp
SAN
San Diego
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SAN
San Diego
17 Apr - 1 May
$318pp
SAN
San Diego
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SAN
San Diego
17 Apr - 1 May
$322pp
SAN
San Diego
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
SAN
San Diego

One-way flights to Chicago Midway from San Diego

6:20 pm - 4:28 am
Delta
1 Stop
8h 08m
SAN - MDW
Delta
$109
Delta
9:57 am - 6:06 pm
Delta
1 Stop
6h 09m
SAN - MDW
Delta
$127
Delta
9:19 am - 6:18 pm
Delta
1 Stop
6h 59m
SAN - MDW
Delta
$139
Delta

Related info for your journey

Flight FAQs

From San Diego to Chicago Midway

Are flight prices decreasing from San Diego 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 San Diego 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 San Diego to Chicago Midway to control the spread of COVID-19?

Delta is one of the many airlines that have implemented additional safety measures to control the spread of COVID-19. Some of the new policies that have been implemented to accommodate travelers flying from San Diego 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 San Diego to Chicago Midway have flexible cancellations due to COVID-19?

Delta, American Airlines, and United Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

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

Yes, there are multiple flights from San Diego to Chicago Midway for under $300. The cheapest flight booked recently is on Delta for just $217, but on average you can expect to pay $265.

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

There are no nonstop flights from San Diego 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 San Diego to Chicago Midway for under $400?

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

What days are nonstop flights available from San Diego to Chicago Midway?

Nonstop flights can be found on the following days: Thursday.

Does it rain more in San Diego or Chicago Midway?

Expected rainfall in San Diego is more than in Chicago Midway. You can expect this to be the case over the next 6 days.

Is San Diego weather warmer or cooler than Chicago Midway?

With an average temperature of 84 °F, peak weather can be found in July. As a traveler, expect to see changes in flight prices during that period. The temperatures in Chicago Midway are hotter than in San Diego.

How long is the flight from San Diego to Chicago Midway?

Departing from San Diego to Chicago Midway will take you 6h 13m.

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

According to our current data, Delta ($217), offers the cheapest pricing from San Diego to Chicago Midway. Delta is priced at 30% lower than the current average price of a flight leaving 3 months from now.

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

The cheapest airline for a one-way flight from San Diego to Chicago Midway is Delta ($109).

Alternative routes for San Diego 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 San Diego

Airports servicing Chicago

Top 4 airlines flying from San Diego to Chicago Midway

Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$171 $289 No cancel fee 65%
American Airlines
$189 $415 No cancel fee 71%
United Airlines
$211 $437 No cancel fee 69%
Delta
$244 $477 No cancel fee N/A

Hourly flight availability from San Diego to Chicago Midway

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