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$75+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
Jan 28 — Feb 41
Tue 1/28
Tue 2/4
1 adult, Economy
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The best prices from San Diego to Chicago are usually found in April or October, booked 54 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 January 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$150
(Cheapflightsfares)

One-way from

$75
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$423

Good round-trip deal

$381 or less

Good one-way deal

$235 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. 7% potential increase in price ($30 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 January 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 January 23, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/79:19 pmSAN - ORD
1 stop5h 55mFrontier
Sun 3/96:45 amORD - SAN
1 stop7h 03mFrontier
Deal found 1/23$150
This Cheapflightsfares deal was found by Cheapflights users on 1/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/101:31 pmSAN - ORD
1 stop14h 00mSpirit Airlines
Wed 2/1210:45 pmORD - SAN
1 stop12h 16mSpirit Airlines
Deal found 1/23$152
This FlightHub deal was found by Cheapflights users on 1/23. 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.
Tue 2/116:25 amSAN - MDW
1 stop15h 52mFrontier
Sun 2/166:40 amMDW - SAN
1 stop19h 40mFrontier
Deal found 1/23$152
This FlightHub deal was found by Cheapflights users on 1/22. 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.
Wed 2/199:56 amSAN - ORD
1 stop9h 54mMultiple Airlines
Fri 2/216:50 amORD - SAN
1 stop19h 30mMultiple Airlines
Deal found 1/22$154
This Kissandfly.com deal was found by Cheapflights users on 1/22. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/157:55 pmSAN - MDW
2 stops13h 33mMultiple Airlines
Sat 2/226:40 amMDW - SAN
1 stop7h 08mMultiple Airlines
Deal found 1/22$195
This American Airlines deal was found by Cheapflights users on 1/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/156:40 amSAN - ORD
Nonstop3h 51mAmerican Airlines
Sat 2/225:45 pmORD - SAN
Nonstop4h 19mAmerican Airlines
Deal found 1/23$238
This Southwest deal was found by Cheapflights users on 1/21. 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.
Sat 2/154:55 pmSAN - MDW
Nonstop3h 50mSouthwest
Sat 2/228:45 pmMDW - SAN
Nonstop4h 30mSouthwest
Deal found 1/21$261
This United Airlines deal was found by Cheapflights users on 1/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/122:14 pmSAN - ORD
Nonstop4h 11mUnited Airlines
Mon 2/177:45 pmORD - SAN
Nonstop4h 45mUnited Airlines
Deal found 1/23$289
This Delta deal was found by Cheapflights users on 1/22. 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.
Tue 2/186:25 amSAN - ORD
1 stop9h 04mDelta
Sun 2/236:15 amORD - SAN
1 stop9h 35mDelta
Deal found 1/22$298
This Delta deal was found by Cheapflights users on 1/22. 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.
Sat 3/86:25 amSAN - MDW
1 stop9h 18mDelta
Sat 3/151:12 pmMDW - SAN
1 stop6h 45mDelta
Deal found 1/22$299
This Mytrip deal was found by Cheapflights users on 1/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/811:40 amSAN - RFD
1 stop7h 06mMultiple Airlines
Sun 5/119:36 pmRFD - SAN
1 stop15h 09mMultiple Airlines
Deal found 1/23$301

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 January 23, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 3/7

9:19 pm-5:14 am

1 stop5h 55m

Chicago O'Hare Intl

Sun 3/9

6:45 am-11:48 am

1 stop7h 03m

$150

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 3/7

9:19 pm-5:31 am

1 stop6h 12m

Chicago Midway

Sun 3/9

6:40 am-11:48 am

1 stop7h 08m

$150

San DiegoChicago

SAN - ORD

SANORD

San Diego

Mon 2/10

1:31 pm-5:31 am

1 stop14h 00m

Chicago O'Hare Intl

Wed 2/12

10:45 pm-9:01 am

1 stop12h 16m

$152

San DiegoChicago

SAN - ORD

SANORD

San Diego

Mon 3/24

8:07 pm-6:36 am

1 stop8h 29m

Chicago O'Hare Intl

Mon 3/31

6:30 am-11:48 am

1 stop7h 18m

$167

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sat 2/15

7:55 pm-11:28 am

2 stops13h 33m

Chicago Midway

Sat 2/22

6:40 am-12:20 am

1 stop19h 40m

$224

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 2/15

6:40 am-12:31 pm

Nonstop3h 51m

Chicago O'Hare Intl

Sat 2/22

5:45 pm-8:04 pm

Nonstop4h 19m

$238

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Wed 2/19

4:50 pm-10:40 pm

Nonstop3h 50m

Chicago Midway

Sat 2/22

8:45 pm-11:15 pm

Nonstop4h 30m

$282

San DiegoChicago

SAN - RFD

SANRFD

San Diego

Thu 3/6

6:15 am-8:47 pm

1 stop12h 32m

Chicago Greater Rockford

Sun 3/9

9:37 pm-7:30 am

1 stop11h 53m

$285

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 2/12

2:14 pm-8:25 pm

Nonstop4h 11m

Chicago O'Hare Intl

Mon 2/17

7:45 pm-10:30 pm

Nonstop4h 45m

$289

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Tue 4/15

10:10 pm-8:42 am

1 stop8h 32m

Chicago Midway

Wed 4/23

3:02 pm-10:30 pm

1 stop9h 28m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Showing 1-10 of 27 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
CheapOairPrice Accuracy2 starsTrust Score*2 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
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 January 17, 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 54 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 January 23, 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 January 21, 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 January 23, 2025.

The most flights from SAN to CHI are scheduled on a Sunday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (21 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 January 23, 2025.
To help decide which airline to fly from San Diego to Chicago, see what other customers have to say about Delta, Spirit Airlines and United Airlines. 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
4,647 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.1
Very good
4,647 reviews
Southwest
8.1
Very good
4,647 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Alaska Airlines
8.0
Very good
9,699 reviews
Southwest
8.1
Very good
4,647 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
8,508 reviews
Southwest
8.1
Very good
4,647 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

United Airlines
7.4
Good
8,970 reviews
Southwest
8.1
Very good
4,647 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,647 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Crew

8.7

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

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 26 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?

    Frontier, at $150, was found to be the cheapest airline from San Diego to Chicago.Alternate airlines to your destination round-trip include Spirit Airlines and American Airlines. You may be able to fly from San Diego to Chicago for 62% 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 $75 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $78 and United Airlines from $119 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 (89%), Iberia (89%), Gulf Air (88%).

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

    On average you can expect to pay $1,146 for a flight from San Diego to Chicago. The cheapest flight overall is $137 while the most popular route, (San Diego - Chicago O'Hare Intl) is currently priced at $110.

  • 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 $53 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 $61 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 January 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$91Average$203FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$95Average$215FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$217Average$434FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$240Average$472FlexibilityNo cancel feeOn-time69%
DeltaCheapest$258Average$370FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$269Average$477FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$391Average$770FlexibilityNo cancel feeOn-time75%
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