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$69+ Cheap flights from San Diego (SAN) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
mar. 2 — mar. 91
dom. 3/2
dom. 3/9
1 adult, Economy
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Find cheap flights from San Diego to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
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3. Compare prices and book
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The best prices from San Diego to Chicago are usually found in October or September, booked 81 days in advance, depart on a Thursday or Wednesday and return on a Tuesday

Cheap flight deals from San Diego to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San Diego (SAN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated febrero 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$147
(FlightHub)

One-way from

$69
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$383

Good round-trip deal

$406 or less

Good one-way deal

$191 or less
Provider with most accurate pricing for San Diego-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Diego-Chicago (CHI) flights.
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From San Diego to Chicago (CHI)
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One-way flight from San Diego to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from San Diego to Chicago (CHI).
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Price to beat on a one-way flight from San Diego to Chicago (CHI).
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Find flight deals from San Diego to Chicago

Cheapest flights from San Diego to Chicago
Explore the most affordable flight options available from San Diego to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 25, 2025.

This FlightHub deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/238:07 pmSAN - ORD
1 stop8h 35mSpirit Airlines
mar. 4/88:00 amORD - SAN
1 stop8h 34mSpirit Airlines
Deal found 2/23$147
This Justfly.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/119:08 pmSAN - ORD
1 stop7h 25mMultiple Airlines
dom. 4/136:45 amORD - SAN
1 stop6h 44mMultiple Airlines
Deal found 2/24$148
This eDestinos deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/86:25 amSAN - MDW
1 stop15h 56mFrontier
mar. 4/156:45 amMDW - SAN
1 stop19h 29mFrontier
Deal found 2/24$160
This CheapOair deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/37:39 pmSAN - ORD
1 stop26h 58mFrontier
dom. 4/67:39 pmORD - SAN
1 stop26h 50mFrontier
Deal found 2/24$174
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/1010:00 pmSAN - ORD
Nonstop4h 07mUnited Airlines
lun. 4/147:50 pmORD - SAN
Nonstop4h 39mUnited Airlines
Deal found 2/25$217
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/236:15 amSAN - MDW
1 stop6h 07mDelta
dom. 4/279:20 amMDW - SAN
1 stop6h 54mDelta
Deal found 2/25$257
This Mytrip deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/246:15 amSAN - RFD
1 stop12h 31mMultiple Airlines
dom. 4/279:36 pmRFD - SAN
1 stop11h 43mMultiple Airlines
Deal found 2/24$257
This Alaska Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/254:12 pmSAN - ORD
2 stops11h 28mAlaska Airlines
mar. 4/16:56 pmORD - SAN
1 stop16h 15mAlaska Airlines
Deal found 2/23$308
This Mytrip deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/67:50 amSAN - MDW
1 stop24h 19mMultiple Airlines
lun. 3/108:40 amMDW - SAN
3 stops24h 50mMultiple Airlines
Deal found 2/24$357
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/255:55 pmSAN - MDW
Nonstop4h 00mSouthwest
lun. 4/288:55 pmMDW - SAN
Nonstop4h 20mSouthwest
Deal found 2/25$361

Find flights from San Diego to Chicago within your budget

Customize your flight search to find flights from San Diego to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated febrero 25, 2025.

Fly from

San Diego

Fly to

Chicago

Route

Depart

Return

Price

San DiegoChicago

SAN - ORD

SANORD

San Diego

dom. 3/23

8:07 pm-6:42 am

1 stop8h 35m

Chicago O'Hare Intl

mar. 4/8

8:00 am-2:34 pm

1 stop8h 34m

$147

San DiegoChicago

SAN - ORD

SANORD

San Diego

vie. 4/11

9:08 pm-6:33 am

1 stop7h 25m

Chicago O'Hare Intl

dom. 4/13

6:45 am-11:29 am

1 stop6h 44m

$148

San DiegoChicago

SAN - MDW

SANMDW

San Diego

mar. 4/8

6:25 am-12:21 am

1 stop15h 56m

Chicago Midway

mar. 4/15

6:45 am-12:14 am

1 stop19h 29m

$160

San DiegoChicago

SAN - ORD

SANORD

San Diego

jue. 4/3

7:39 pm-12:37 am

1 stop26h 58m

Chicago O'Hare Intl

dom. 4/6

7:39 pm-8:29 pm

1 stop26h 50m

$174

San DiegoChicago

SAN - ORD

SANORD

San Diego

jue. 4/10

10:00 pm-4:07 am

Nonstop4h 07m

Chicago O'Hare Intl

lun. 4/14

7:50 pm-10:29 pm

Nonstop4h 39m

$217

San DiegoChicago

SAN - MDW

SANMDW

San Diego

mié. 4/23

6:15 am-2:22 pm

1 stop6h 07m

Chicago Midway

dom. 4/27

9:20 am-2:14 pm

1 stop6h 54m

$257

San DiegoChicago

SAN - RFD

SANRFD

San Diego

jue. 4/24

6:15 am-8:46 pm

1 stop12h 31m

Chicago Greater Rockford

dom. 4/27

9:36 pm-7:19 am

1 stop11h 43m

$257

San DiegoChicago

SAN - ORD

SANORD

San Diego

mar. 3/25

4:12 pm-5:40 am

2 stops11h 28m

Chicago O'Hare Intl

mar. 4/1

6:56 pm-9:11 am

1 stop16h 15m

$308

San DiegoChicago

SAN - MDW

SANMDW

San Diego

jue. 3/6

7:50 am-10:09 am

1 stop24h 19m

Chicago Midway

lun. 3/10

8:40 am-7:30 am

3 stops24h 50m

$357

San DiegoChicago

SAN - MDW

SANMDW

San Diego

vie. 4/25

5:55 pm-11:55 pm

Nonstop4h 00m

Chicago Midway

lun. 4/28

8:55 pm-11:15 pm

Nonstop4h 20m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/24

Showing 1-10 of 25 results
1
2
3

Compare providers for flights from San Diego to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Diego to Chicago in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on San Diego-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Diego-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Diego-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Diego-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Diego-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from San Diego to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San Diego with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from San Diego to Chicago

Get recent, data-driven insights about flights from San Diego to Chicago including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a round-trip flight from San Diego to Chicago. Price data was last updated on February 25, 2025.

The price you pay for your flight from San Diego to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 81 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from San Diego to Chicago?

Currently, August is the cheapest month in which you can book a flight from San Diego to Chicago (average of $245). Flying from San Diego to Chicago in March is currently the most expensive (average of $322). 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.

What is the cheapest time of day to fly from SAN to CHI?

Find hourly flight availability from San Diego to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated febrero 25, 2025.

It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 20% on the cost of your flight, compared to a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from San Diego to Chicago. Price data was last updated on February 23, 2025.

Travelers seeking maximum savings on their San Diego to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from San Diego to Chicago

Explore weekly flight availability from San Diego to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated febrero 25, 2025.

The most flights from SAN to CHI are scheduled on a Tuesday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated febrero 25, 2025.
To help decide which airline to fly from San Diego to Chicago, see what other customers have to say about Southwest, Alaska Airlines and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,374 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Southwest
8.1
Very good
4,374 reviews
Southwest
8.1
Very good
4,374 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Alaska Airlines
8.0
Very good
9,713 reviews
Southwest
8.1
Very good
4,374 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Delta
8.0
Very good
8,163 reviews
Southwest
8.1
Very good
4,374 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

United Airlines
7.4
Good
8,734 reviews
Southwest
8.1
Very good
4,374 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Allegiant Air
7.3
Good
759 reviews
Southwest
8.1
Very good
4,374 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Related info for your journey

Find useful and relevant information for your journey from San Diego to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 21 flights from San Diego to Chicago per day from 7 different airlines.

  • What are the cheapest airlines flying from San Diego to Chicago round-trip?

    Spirit Airlines, at $147, was found to be the cheapest airline from San Diego to Chicago.Alternate airlines to your destination round-trip include Frontier and Delta. You may be able to fly from San Diego to Chicago for 63% less than the average price by searching for these airlines.

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

    One-way options have recently been found by users for as low as $69 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $71 and Allegiant Air from $108 one-way.

  • What are the most popular routes from San Diego to Chicago?

    While some choose either San Diego - Chicago Midway or San Diego - Chicago Greater Rockford, San Diego - Chicago O'Hare Intl is the most popular route from San Diego to Chicago.

  • What are the most reliable airlines from San Diego to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from San Diego to Chicago on time: Qatar Airways (87%), Emirates (87%), SWISS (87%).

  • What are the cheapest flights from San Diego to Chicago?

    On average you can expect to pay $945 for a flight from San Diego to Chicago. The cheapest flight overall is $141 while the most popular route, (San Diego - Chicago O'Hare Intl) is currently priced at $99.

  • Where are the most common layover locations when flying from San Diego to Chicago?

    San Diego to Chicago flights have a layover in Las Vegas most of the time. Denver sees the next most layovers on San Diego to Chicago flights.

  • What are some popular things to do or see while on a layover in Las Vegas?

    The majority of Las Vegas visitors spend their time at Fremont Street Experience, Colosseum at Caesars Palace, and Stratosphere Tower. Fremont Street Experience, Colosseum at Caesars Palace, and Stratosphere Tower can be accessed by traveling approximately 5.9 mi, 2.6 mi, and 4.3 mi, respectively from Las Vegas Harry Reid Intl. Travelers can rent a car at Las Vegas Harry Reid Intl for an average daily rate of $49 to make sightseeing during their layover a little easier.

  • What are some popular points of interest to see during a layover in Denver?

    The majority of Denver visitors spend their time at Coors Field, 16th Street Mall, and Paramount Theatre. Coors Field, 16th Street Mall, and Paramount Theatre are located about 18.4 mi, 18.7 mi, and 18.6 mi, respectively from Denver Intl. Travelers can rent a car at Denver Intl for an average daily rate of $48 to make sightseeing during their layover a little easier.

  • Where are the least popular layover locations for San Diego to Chicago flights?

    Flights departing from San Diego and landing in Chicago layover in Phoenix least frequently.

  • Can I find deals for flights from San Diego to Chicago that include hotel bookings?

    Yes. In addition to deals on San Diego to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Diego to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Diego to Chicago.

  • Can I find deals for business class flights from San Diego to Chicago?

    Yes. Cheapflights offers flight deals from San Diego to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Diego to Chicago?

    Currently, August is the cheapest month in which you can book a flight from San Diego to Chicago (average of $245). Flying from San Diego to Chicago in March is currently the most expensive (average of $322). 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.

See more FAQs

Traveling to a place near San Diego?

Book flights to San Diego if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for San Diego to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from San Diego to Chicago

Discover the top 7 airlines that operate flights from San Diego to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated febrero 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$91Average$204FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$93Average$199FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$217Average$431FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$241Average$472FlexibilityNo cancel feeOn-time69%
DeltaCheapest$258Average$380FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$332Average$478FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$391Average$784FlexibilityNo cancel feeOn-time75%
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