Flights from San Diego to Chicago

Search and find cheap flights from San Diego to Chicago (United States, North America)
Search and find cheap flights from San Diego to Chicago (United States, North America)

Looking for the best tickets for San Diego to Chicago?

Look no more. We’ve gone through the latest 754,672 fares to bring you all the insights you could possibly want.
Expect to pay
269 USD for flights from San Diego to Chicago leaving on 6/5/2017 and returning on 7/7/2017
Low 96 USD
269 USD
High 446 USD
Choose my own dates
Best time to book
Cheapest time to buy a ticket for San Diego — Chicago is approximately 58 days to departure.
Normally the best deals on San Diego to Chicago flights are available 2 to 4 months prior to departure.
Days before departure
Best month
Cheapest time of year to fly to Chicago from San Diego is January and February. Most expensive are November and December.
Currently the cheapest days to fly this route are between June and July.
Impact on price
Cheapest airline
According to our data, Spirit Airlines, Frontier Airlines and Major US Carrier are the cheapest airlines to fly this route.
Popular airlines for this route are Spirit Airlines, Frontier Airlines and Major US Carrier.
Impact on price (additional fees may apply)
Spirit Airlines
+1%
Frontier Airlines
+23%
Major US Carrier
+26%
United Airlines
+29%
Delta Air Lines
+29%
American Airlines
+31%
Best time to fly
San Diego to Chicago flights are approximately 5% more expensive in the morning than in the afternoon.
It's generally cheaper to take afternoon flights from San Diego to Chicago.
Impact on price
Cheapest day
Cheapest day of week is typically Monday and the most expensive is typically Sunday.
Sunday is normally the most expensive day to fly, whilst Monday tends to be the cheapest.
Impact on price
Cheapest route
Fly Lindberg Fld - Midway for the best San Diego to Chicago flight prices saving up to 0% on average.
Of the possible routes between San Diego and Chicago best prices tend to be found on Lindberg Fld - Midway.
We've got 43 booking sites supporting this and nearby routes.
Impact on price
Lindberg Fld-Midway
+0%
Lindberg Fld-O'Hare Intl
+2%
Direct flights
There are direct flights from Lindberg Fld to Chicago all week with a flight time of 3 hours 54 minutes.
Direct flights available: 357 PER WEEK
Popular non-direct routes for this connection are Lindberg Fld - Detroit Metro - Midway, Lindberg Fld - Salt Lake City Intl - O'Hare Intl and Lindberg Fld - Saint Paul Intl - Midway.
Stop-off cities for indirect flights from Lindberg Fld to Chicago include Detroit Metro, Salt Lake City Intl and Saint Paul Intl.
Direct flights available on
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Get there quickly

Direct flights to Chicago from San Diego
Return trip
Apr 6 - Apr 17
233 USD
OneTravel
SAN SAN
4h 6min
Direct
CHI CHI
CHI CHI
4h 20min
Direct
SAN SAN
Return trip
Apr 6 - Apr 9
283 USD
OneTravel
SAN SAN
4h 6min
Direct
CHI CHI
CHI CHI
4h 20min
Direct
SAN SAN
Return trip
Mar 31 - Apr 1
445 USD
CrystalTravelUS
SAN SAN
3h 50min
Direct
CHI CHI
CHI CHI
4h 15min
Direct
SAN SAN

Go right away

Last minute flights from San Diego to Chicago
Return trip
Apr 6 - Apr 17
233 USD
OneTravel
SAN SAN
4h 6min
Direct
CHI CHI
CHI CHI
4h 20min
Direct
SAN SAN
Return trip
Apr 6 - Apr 9
283 USD
OneTravel
SAN SAN
4h 6min
Direct
CHI CHI
CHI CHI
4h 20min
Direct
SAN SAN
Return trip
Apr 4 - Apr 6
310 USD
KissAndFlyUS
SAN SAN
9h 0min
1 stop
CHI CHI
CHI CHI
4h 27min
Direct
SAN SAN

Go for less - experience more

Cheap flights from San Diego to Chicago
Return trip
Apr 13 - Apr 17
213 USD
OneTravel
SAN SAN
4h 6min
Direct
CHI CHI
CHI CHI
4h 20min
Direct
SAN SAN
Return trip
Apr 13 - Apr 19
306 USD
KiwiUS
SAN SAN
3h 50min
Direct
CHI CHI
CHI CHI
9h 3min
1 stop
SAN SAN
Return trip
Apr 13 - Apr 16
307 USD
Smartfares
SAN SAN
13h 57min
2 stops
CHI CHI
CHI CHI
4h 20min
Direct
SAN SAN

Coming or going?

Cheap flights from Chicago to San Diego
Return trip
Mar 30 - Apr 4
253 USD
CFOneTravel
CHI CHI
4h 30min
Direct
SAN SAN
SAN SAN
11h 51min
1 stop
CHI CHI
Return trip
Mar 30 - May 1
480 USD
CheapTickets
CHI CHI
6h 14min
1 stop
SAN SAN
SAN SAN
7h 59min
1 stop
CHI CHI
Return trip
Mar 30 - Apr 2
527 USD
OneTravel
CHI CHI
4h 30min
Direct
SAN SAN
SAN SAN
9h 21min
2 stops
CHI CHI

Weather forecast for Chicago

Going soon? Be prepared for the weather in Chicago.

So what's it going to cost once you're in Chicago

Compare the costs of everyday items in San Diego and Chicago
CAPPUCCINO
Regular
San Diego
3.81 USD
-4%
Chicago
3.95 USD
Cappuccino is 3.7% more expensive in Chicago than San Diego
MEAL
Inexpensive
San Diego
14.55 USD
-3%
Chicago
14.98 USD
Meal is 2.9% more expensive in Chicago than San Diego
MILK
1 liter
San Diego
3.48 USD
17%
Chicago
2.9 USD
Milk is 17% cheaper in Chicago than San Diego
BUS
One-way ticket
San Diego
2.51 USD
10%
Chicago
2.25 USD
Bus is 10% cheaper in Chicago than San Diego
MOVIE THEATER
1 ticket
San Diego
12.55 USD
5%
Chicago
11.98 USD
movie theater is 4.5% cheaper in Chicago than San Diego
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