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Cheap flights San Diego — Chicago

San Diego (SAN, US) Chicago (CHI, US)
from $106 2 786 km ~3h 47m 11 flights found 2 airlines cheapest on Saturday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $106 on 10.01.2027
Prices shown are from searches by other travellers over the last 24 hours. Missing a date? Click any day — we'll find tickets anyway.
November 2026
Mo
Tu
We
Th
Fr
Sa
Su
December 2026
Mo
Tu
We
Th
Fr
Sa
Su
January 2027
Mo
Tu
We
Th
Fr
Sa
Su
Prices found for 19 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
11 Jan 2027, Mon
American Airlines AA 830
09:31
SAN San Diego International Airport
13:39
ORD O'Hare International Airport
4h 8m Direct
Farera
$106
View this ticket
19 Jan 2027, Tue
Frontier Airlines F9 1470
01:38
SAN San Diego International Airport
08:22
MDW Chicago Midway International Airport
6h 44m 2 stops
Tickets
$133
View this ticket
14 Nov 2026, Sat
Frontier Airlines F9 2818
17:25
SAN San Diego International Airport
22:25
ORD O'Hare International Airport
5h 1 stop
Farera
$136
View this ticket
19 Jan 2027, Tue
American Airlines AA 830
09:31
SAN San Diego International Airport
13:39
ORD O'Hare International Airport
4h 8m Direct
Farera
$172
View this ticket
15 Nov 2026, Sun
American Airlines AA 2556
00:29
SAN San Diego International Airport
04:59
ORD O'Hare International Airport
4h 30m Direct
Farera
$180
View this ticket
04 Jan 2027, Mon
Frontier Airlines F9 1326
06:38
SAN San Diego International Airport
11:52
ORD O'Hare International Airport
5h 14m 1 stop
Kiwi.com
$186
View this ticket
Route characteristics
Distance
2 786 km
Flight time
3h 47m
Time difference
+2h
Minimum price
from $106 (10.01.2027)
Average price
$138
Maximum price
$186
Departures per week
1
Cheapest day
Saturday
Departure airports (1)
SAN San Diego International Airport
Arrival airports (2)
MDW Chicago Midway International Airport ORD O'Hare International Airport
Airlines (2)
AA American Airlines F9 Frontier Airlines
Agencies (4)
Farera Tickets Flightnetwork Kiwi.com
Prices by day of week
Monday
$106
avg $146
Tuesday
$133
avg $153
Saturday
$136
avg $136
Cheapest
Sunday
$180
avg $180
Price trend by month
November 2026
from $136
avg $158
2 flights
January 2027
from $106
avg $149
4 flights
Airlines — cheapest prices 2
American Airlines
American Airlines
6 flights · 6 days
$106
Frontier Airlines
Frontier Airlines
Low-cost 5 flights · 5 days
$133
Where to buy tickets 4
Farera
8 tickets · 7 days
from $106
Tickets
1 tickets · 1 days
from $133
Flightnetwork
1 tickets · 1 days
from $150
Kiwi.com
1 tickets · 1 days
from $186
Airports

From — San Diego (1)

  • SAN San Diego International Airport

To — Chicago (2)

  • MDW Chicago Midway International Airport
  • ORD O'Hare International Airport
Other destinations from San Diego
Los Angeles
US · Hub
Dallas
US · Hub
Portland
US
Puerto Vallarta
MX
Seattle
US
Calgary
CA
Vancouver
CA
Fresno
US
Honolulu
US
Monterey
US
Kahului
US
San Jose Del Cabo
MX
Frequently asked questions about the route San Diego — Chicago
How long is the flight from San Diego to Chicago?
Approximate flight time — 3h 47m. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from San Diego to Chicago?
The straight-line distance — 2 786 km.
How much do flights from San Diego to Chicago cost?
The minimum price over 3 months — from $106 on 10.01.2027.
What is the average ticket price?
The average price — $138. Range: $106 — $186.
What is the time difference between San Diego and Chicago?
The difference — +2h.
From which airports does San Diego operate flights?
From San Diego: SAN (San Diego International Airport).
To which airports in Chicago do flights arrive?
To Chicago: MDW (Chicago Midway International Airport), ORD (O'Hare International Airport).
Which airlines fly this route?
This route is served by 2 airlines: American Airlines, Frontier Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $106. Total direct flights found: 3.
Which day of the week is cheapest?
The cheapest day of the week — Saturday.
When is the best time to buy tickets?
Optimal — 1–3 months before departure. Check the calendar above — it shows the best dates.
How do I book flights?
Click "View this ticket" on any flight card — you'll be redirected to the booking page with this specific ticket pre-selected.
About the route San Diego — Chicago

Flights San Diego — Chicago is a popular route. The straight-line distance is 2 786 km. Flight time 3h 47m. Time difference +2h.

From San Diego (SAN) flights depart from 1 airport: SAN. To Chicago (CHI) — 2 arrival airports: MDW, ORD.

2 airlines operate on this route: American Airlines, Frontier Airlines.

The minimum price for the next 3 months — from $106 (10.01.2027). The cheapest dates are highlighted in the calendar above.

The average ticket price — $138, ranging from $106 to $186. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Saturday.

Other destinations in United States from San Diego
Los Angeles
US
Dallas
US
Portland
US
Seattle
US
Fresno
US
Honolulu
US
Monterey
US
Kahului
US

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