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Cheap flights from California to Chicago from $39

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from California to Chicago departing on 9/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Allegiant Air Logo
3:22 pm - 8:52 pmLAS-MDW
3h 30mnonstop
Allegiant Air Logo
7:03 pm - 8:48 pmMDW-LAS
3h 45mnonstop
$78Allegiant Air
Find Deal
Fri, Sep 26 - Mon, Sep 29
Southwest Logo
10:40 am - 4:40 pmSAN-MDW
4h 00mnonstop
Southwest Logo
7:25 pm - 9:35 pmMDW-SAN
4h 10mnonstop
$139Southwest
Find Deal
Wed, Sep 24 - Sat, Sep 27
Logo
6:30 am - 8:52 pmOAK-MDW
12h 22m1 stop
Logo
7:03 pm - 11:32 pmMDW-OAK
6h 29m1 stop
$143
Find Deal
Fri, Sep 26 - Mon, Sep 29
Southwest Logo
10:40 am - 4:40 pmSAN-MDW
4h 00mnonstop
Southwest Logo
7:05 pm - 9:20 pmMDW-SAN
4h 15mnonstop
$148Southwest
Find Deal
Wed, Aug 27 - Wed, Sep 3
Southwest Logo
8:00 am - 1:55 pmSAN-MDW
3h 55mnonstop
Southwest Logo
7:05 pm - 9:20 pmMDW-SAN
4h 15mnonstop
$154Southwest
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Wed, Aug 27 - Wed, Sep 3
Logo
12:55 am - 10:28 amLAS-MDW
7h 33m1 stop
Logo
7:03 pm - 8:48 pmMDW-LAS
3h 45mnonstop
$157
Find Deal
Fri, Sep 26 - Mon, Sep 29
Frontier Logo
10:48 am - 10:20 pmLAS-MDW
9h 32m1 stop
Frontier Logo
12:35 pm - 7:15 pmMDW-LAS
8h 40m1 stop
$211Frontier
Find Deal
Fri, Aug 15 - Mon, Aug 18
Frontier Logo
11:04 pm - 9:18 amLAS-MDW
8h 14m1 stop
Frontier Logo
4:48 pm - 8:21 pmMDW-LAS
5h 33m1 stop
$212Frontier
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Sat, Sep 27 - Mon, Sep 29
Delta Logo
10:25 pm - 8:35 amLAX-MDW
8h 10m1 stop
Delta Logo
6:00 am - 11:58 amMDW-LAX
7h 58m1 stop
$217Delta
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Sat, Aug 30 - Sat, Sep 6
Delta Logo
11:30 pm - 8:53 amLAX-MDW
7h 23m1 stop
Delta Logo
7:15 pm - 11:49 pmMDW-LAX
6h 34m1 stop
$218Delta
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Fri, Sep 19 - Tue, Sep 23

Southwest flights from California to Chicago Midway Airport

Our best Southwest deals on California to Chicago Midway Airport flight tickets
Southwest
Sep 24
SAN10:40 amSan Diego
4h 00m
MDW4:40 pmChicago Midway
Sep 27
MDW7:25 pmChicago Midway
4h 10m
SAN9:35 pmSan Diego
$139
Find similar
Southwest
Aug 27
SAN10:40 amSan Diego
4h 00m
MDW4:40 pmChicago Midway
Sep 3
MDW7:05 pmChicago Midway
4h 15m
SAN9:20 pmSan Diego
$148
Find similar
Southwest
Aug 27
SAN8:00 amSan Diego
3h 55m
MDW1:55 pmChicago Midway
Sep 3
MDW7:05 pmChicago Midway
4h 15m
SAN9:20 pmSan Diego
$154
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Delta flights from California to Chicago Midway Airport

Our best Delta deals on California to Chicago Midway Airport flight tickets
Delta
Aug 30
LAX10:25 pmLos Angeles
8h 10m
1 stop
MDW8:35 amChicago Midway
Sep 6
MDW6:00 amChicago Midway
7h 58m
1 stop
LAX11:58 amLos Angeles
$217
Find similar
Delta
Sep 19
LAX11:30 pmLos Angeles
7h 23m
1 stop
MDW8:53 amChicago Midway
Sep 23
MDW7:15 pmChicago Midway
6h 34m
1 stop
LAX11:49 pmLos Angeles
$218
Find similar
Delta
Aug 22
LAX12:35 amLos Angeles
6h 16m
1 stop
MDW8:51 amChicago Midway
Aug 30
MDW1:08 pmChicago Midway
6h 39m
1 stop
LAX5:47 pmLos Angeles
$233
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momondo Fare Finder

 
Customize your flight search to find flights from California to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated August 1, 2025.
Use the filters below to find and compare flights from California to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Las VegasChicago

LAS - MDW

LASMDW

Las Vegas Harry Reid Intl

Fri 9/26

3:22 pm-8:52 pm

Nonstop3h 30m

Chicago Midway

Mon 9/29

7:03 pm-8:48 pm

Nonstop3h 45m

$78

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 9/24

10:40 am-4:40 pm

Nonstop4h 00m

Chicago Midway

Sat 9/27

7:25 pm-9:35 pm

Nonstop4h 10m

$139

OaklandChicago

OAK - MDW

OAKMDW

Oakland

Fri 9/26

6:30 am-8:52 pm

1 stop12h 22m

Chicago Midway

Mon 9/29

7:03 pm-11:32 pm

1 stop6h 29m

$143

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 8/27

10:40 am-4:40 pm

Nonstop4h 00m

Chicago Midway

Wed 9/3

7:05 pm-9:20 pm

Nonstop4h 15m

$148

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 8/27

8:00 am-1:55 pm

Nonstop3h 55m

Chicago Midway

Wed 9/3

7:05 pm-9:20 pm

Nonstop4h 15m

$154

Las VegasChicago

LAS - MDW

LASMDW

Las Vegas Harry Reid Intl

Fri 9/26

12:55 am-10:28 am

1 stop7h 33m

Chicago Midway

Mon 9/29

7:03 pm-8:48 pm

Nonstop3h 45m

$157

Las VegasChicago

LAS - MDW

LASMDW

Las Vegas Harry Reid Intl

Fri 8/15

10:48 am-10:20 pm

1 stop9h 32m

Chicago Midway

Mon 8/18

12:35 pm-7:15 pm

1 stop8h 40m

$211

Las VegasChicago

LAS - MDW

LASMDW

Las Vegas Harry Reid Intl

Sat 9/27

11:04 pm-9:18 am

1 stop8h 14m

Chicago Midway

Mon 9/29

4:48 pm-8:21 pm

1 stop5h 33m

$212

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Sat 8/30

10:25 pm-8:35 am

1 stop8h 10m

Chicago Midway

Sat 9/6

6:00 am-11:58 am

1 stop7h 58m

$217

Los AngelesChicago

LAX - MDW

LAXMDW

Los Angeles

Fri 9/19

11:30 pm-8:53 am

1 stop7h 23m

Chicago Midway

Tue 9/23

7:15 pm-11:49 pm

1 stop6h 34m

$218

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from California to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from California, with most prices found around $268. If you are unable to visit Chicago Midway Airport during the month of January, then departing from California during the month February is also very affordable. Most momondo users find prices during this month for around $281.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from California. The lowest ticket price found for a Saturday departure recently was $368. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from California because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $494.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from California in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $318 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $474. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest California to Chicago Midway flight route?

Fly from San Diego to Chicago Midway for the best California - Chicago Midway flight prices

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

You are more likely to see cheaper flights to Chicago Midway Airport from California when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $330 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from California for as low as $244 on momondo.

What cabin class options are available on California to Chicago Midway flights?

There are 1 cabin classes available to choose from on California to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on California to Chicago Midway Airport flights?

You could potentially save up to 16% on your flight if you consider stops on a California to Chicago Midway Airport flight.

Cheap California to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from California to Chicago Midway Airport

Best Price Found

$39

Fastest flight time

3h 25m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from California in the past 72 hours is $39. The best round-trip flight deal from California to Chicago Midway Airport found on momondo in the last 72 hours is $78.
The fastest flight from California to Chicago Midway Airport takes 3h 25m
Direct flights go from California to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from California to Chicago Midway Airport?

    Prices for flights from California to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from California to Chicago Midway Airport?

  • How old do you have to be to fly from California to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from California to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from California to Chicago Midway Airport?

Best airlines flying from California to Chicago Midway Airport

Compare and see reviews for airlines that fly from California to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $67Free CancellationRating
6.3
8,048 reviews
Search Spirit Airlines flights
FrontierPriceFrom $110Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
United AirlinesPriceFrom $133Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
SouthwestPriceFrom $191Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
American AirlinesPriceFrom $197Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $197Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
DeltaPriceFrom $236Free CancellationRating
8.0
7,981 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from California to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from California to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from California to Chicago with flexible booking policies on momondo?

All flight searches from California to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from California to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from California to Chicago.

I’m not ready to book a flight from California to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from California are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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