Cheap flights from San Diego to Chicago (SAN - CHI)

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The best prices from San Diego to Chicago are usually found in August or July, booked 21 days in advance, depart on a Thursday or Wednesday and return on a Tuesday

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

All the information you need to plan the best SAN to CHI flight in 2021: compare San Diego to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
SAN - CHI
Price
$74 - $313
CHI
Temperature
33.8 - 84.2 °F
CHI
Precipitation
0.7 - 4.3 inches

Popular in

December

High demand for flights, 34% potential price rise

Cheapest in

August

Best time to find cheap flights, 64% potential price drop

Round-trip from

$74

From San Diego to Chicago

One-way from

$49

One-way flight from San Diego to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from San Diego to Chicago?

Departing on a Wednesday is a good option for securing a great price. You can expect to save up to 26% when planning your travel around this day of the week.

How far in advance should I book a flight from San Diego to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 18 days in advance, which can save you up to 11% on flights from San Diego to Chicago compared to booking the week you need them. Waiting 18 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $189. For sooner than that we have options available in the next 3 days from $217.

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

The best pricing can be found in the month of August. Prices to Chicago from San Diego average $205. You can even find prices in August for less than $205, as users have found deals to Chicago from as low as $35. The month of December appears to be one of the more expensive times to travel to Chicago from San Diego. Flying in the targeted month can save you up to 52%.

When is the cheapest time to fly from San Diego to Chicago (SAN - CHI)?

It’s optimal to fly from San Diego to Chicago at noon. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight in the morning.

Cheap flights from San Diego to Chicago in September, October 2021

The best prices found for SAN to CHI flights for September, October
22 Sep - 29 Sep
$42pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
SAN
San Diego
24 Sep - 29 Sep
$50pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
SAN
San Diego
1 Oct - 4 Oct
$54pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SAN
San Diego

San Diego to Chicago 2021 flight deals

Cheap flights to Chicago from San Diego found for this year
12 Nov - 15 Nov
$42pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
SAN
San Diego
11 Nov - 14 Nov
$45pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
SAN
San Diego
24 Sep - 29 Sep
$50pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
SAN
San Diego

Non-stop flights to Chicago from San Diego

Save time with San Diego to Chicago direct flight deals
12 Nov - 15 Nov
$42pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
SAN
San Diego
11 Nov - 14 Nov
$45pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
SAN
San Diego
24 Sep - 29 Sep
$50pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
SAN
San Diego

Last minute flights from San Diego to Chicago

Late deals on round-trip flights to Chicago from San Diego, departing today and this week
22 Sep - 29 Sep
$42pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
SAN
San Diego
24 Sep - 29 Sep
$50pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
SAN
San Diego
22 Sep - 25 Sep
$54pp
SAN
San Diego
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
SAN
San Diego

One-way flights to Chicago from San Diego

The cheapest one-way flights from San Diego to Chicago
6:29 pm - 12:20 am
United Airlines
Nonstop
3h 51m
SAN - ORD
United Airlines
$49
United
10:00 am - 7:10 pm
Multiple Airlines
1 Stop
7h 10m
SAN - ORD
Multiple Airlines
$57
Kiwi.com
4:13 pm - 12:57 am
Frontier
1 Stop
6h 44m
SAN - ORD
Frontier
$59
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">San Diego</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From San Diego to Chicago

What airport do you fly from for flights from San Diego to Chicago?

If you book a flight to Chicago from San Diego, you will be flying from San Diego, which is the city’s only airport. San Diego (SAN) is located 2.6 mi from the center of San Diego. There are 39 flights from San Diego to Chicago per day from 8 different airlines.

Which airlines flying from San Diego to Chicago have flexible cancellations due to COVID-19?

Spirit Airlines, 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.

Are flight prices decreasing from San Diego to Chicago 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 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.

Can I find flights from San Diego to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from San Diego to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $40, but on average you can expect to pay $60.

Are there nonstop flights from San Diego to Chicago for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from San Diego to Chicago under $100. A good price for a nonstop flight from San Diego to Chicago is less than $71.

Are there last-minute flights available from San Diego to Chicago for under $100?

There are currently 20+ open flights from San Diego to Chicago within the next 7 days for less than $100.

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

You can find nonstop flights on the following days: Monday, Thursday, Saturday.

How many flights depart from San Diego to Chicago on average per day?

Travelers can expect 5 flights from San Diego to Chicago on average per day.
Morning (6am - Noon) - 20% of flight departures
Afternoon (Noon - 6pm) - 40% of flight departures
Evening (6pm - Midnight) - 40% of flight departures

How long is the flight from San Diego to Chicago?

For as low as $40, Spirit Airlines can have you in Chicago from San Diego in 3h 57m. The distance from San Diego to Chicago is about 1729 mi. All flights are typically nonstop.

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

Flying on Spirit Airlines is currently your cheapest option to Chicago, with prices starting at $40. Spirit Airlines is currently priced 80% below the average price you’ll pay for this route.

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

$19 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on United Airlines and Frontier, with prices starting from $49 and $58, respectively.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from San Diego?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from San Diego need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from San Diego must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from San Diego are not required to quarantine after entering Chicago.

Do I need a test to fly back to San Diego from Chicago?

Returning to San Diego from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to San Diego.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering San Diego.

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for San Diego to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from San Diego to Chicago.
Flight duration from SAN to Chicago
4h 11m
Average temperature for September in Chicago
77.0 °F
Avg rainfall for September in Chicago
2.4 ″

Airports servicing San Diego

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from San Diego to Chicago

The chart below displays the airlines Cheapflights users traveling from San Diego to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$101 $202 No cancel fee 62%
Spirit Airlines
$100 $258 No cancel fee 65%
American Airlines
$105 $353 No cancel fee 71%
Delta
$122 $362 No cancel fee N/A
United Airlines
$115 $371 No cancel fee 69%
Alaska Airlines
$134 $449 No cancel fee 75%

Hourly flight availability from San Diego to Chicago

See what time of day planes typically take off from San Diego towards Chicago.
Morning 6 AM to noon 62% of SAN to CHI departures
Early morning Midnight to 6 AM 19% of SAN to CHI departures
Afternoon Noon to 6 PM 12% of SAN to CHI departures
Evening 6 PM to midnight 7% of SAN to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from San Diego to Chicago
See how many times per day planes take to the skies headed from San Diego to Chicago.
Sunday
39 daily flights
Monday
42 daily flights
Tuesday
31 daily flights
Wednesday
54 daily flights
Thursday
44 daily flights
Friday
48 daily flights
Saturday
21 daily flights
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