For shorter lines, head to the Tom Bradley International Terminal, especially in the morning and midday hours.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $169 (Kiwi.com) |
One-way from | $87 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $307 |
Good round-trip deal | $313 or less |
Good one-way deal | $195 or less |
Fly from
Fly to
Route
Depart
Return
Price
Los AngelesChicago
LAX - MDW
LAXMDW
Los Angeles
Sat 12/13
6:15 am-3:44 pm
1 stop7h 29m
Chicago Midway
Tue 12/16
1:14 pm-5:55 pm
1 stop6h 41m
Los AngelesChicago
LAX - MDW
LAXMDW
Los Angeles
Sun 12/14
2:15 pm-11:47 pm
1 stop7h 32m
Chicago Midway
Tue 12/16
12:50 pm-8:40 pm
1 stop9h 50m
Los AngelesChicago
LAX - MDW
LAXMDW
Los Angeles
Wed 12/10
7:15 am-4:34 pm
1 stop7h 19m
Chicago Midway
Tue 12/16
1:14 pm-5:55 pm
1 stop6h 41m
Los AngelesChicago
LAX - MDW
LAXMDW
Los Angeles
Mon 12/15
2:15 pm-11:47 pm
1 stop7h 32m
Chicago Midway
Wed 12/17
10:49 am-4:42 pm
1 stop7h 53m
Los AngelesChicago
LAX - MDW
LAXMDW
Los Angeles
Fri 12/12
10:59 pm-9:54 am
1 stop8h 55m
Chicago Midway
Sun 12/14
5:13 pm-12:54 am
1 stop9h 41m
Los AngelesChicago
LAX - MDW
LAXMDW
Los Angeles
Thu 12/4
6:00 am-12:05 pm
Nonstop4h 05m
Chicago Midway
Thu 12/11
8:10 am-10:45 am
Nonstop4h 35m
Los AngelesChicago
LAX - MDW
LAXMDW
Los Angeles
Fri 11/14
3:15 pm-9:10 pm
Nonstop3h 55m
Chicago Midway
Mon 11/17
4:15 pm-6:40 pm
Nonstop4h 25m
Los AngelesChicago
LAX - MDW
LAXMDW
Los Angeles
Wed 12/3
11:00 pm-5:00 am
Nonstop4h 00m
Chicago Midway
Sat 12/6
9:40 am-3:35 pm
1 stop7h 55m
Los AngelesChicago
LAX - MDW
LAXMDW
Los Angeles
Thu 12/4
11:25 am-9:00 pm
1 stop7h 35m
Chicago Midway
Sun 12/7
6:05 am-8:35 am
Nonstop4h 30m
Los AngelesChicago
LAX - MDW
LAXMDW
Los Angeles
Mon 11/17
11:00 pm-5:00 am
Nonstop4h 00m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars |
Booking 59 days in advance of your planned departure date is, on average, the best time to get cheap flights from Los Angeles to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, November is the cheapest month in which you can book a flight from Los Angeles to Chicago Midway Airport (average of $134). Flying from Los Angeles to Chicago Midway Airport in December is currently the most expensive (average of $214). 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.
It’s typically best to fly out from Los Angeles to Chicago Midway Airport in the afternoon. Doing so could potentially save you 36% on the flight price compared to flying at noon, which is usually more expensive.
Travelers seeking maximum savings on their Los Angeles to Chicago Midway Airport flight should consider departing on Monday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
About 10% of weekly flights between Los Angeles and Chicago have experienced delays in the past year, with the average delay time being 135 minutes.
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
Saturday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Southwest have had the lowest number of delays on this route, with just 10% of flights being delayed.
Overall
Crew
Food
Entertainment
Comfort
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Overall
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Food
Entertainment
Comfort
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Reviews
Walter,Aug 2025
OAK - SAN
Overall
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Food
Entertainment
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Reviews
Walter,Aug 2025
OAK - SAN
Overall
Crew
Food
Entertainment
Comfort
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Overall
Crew
Food
Entertainment
Comfort
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Overall
Crew
Food
Entertainment
Comfort
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$215 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$130 | Average$267 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$206 | Average$343 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$224 | Average$345 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$226 | Average$338 | FlexibilityNo cancel fee | On-timeN/A |