Chicago

$88+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
Jan 3 — Jan 101
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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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Cheapflights Tip: The best prices from San Diego to Chicago are usually found in October or September, booked 44 days in advance, depart on a Wednesday or Thursday and return on a Friday

Cheap 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 December 4, 2025.

This American Airlines deal was found by Cheapflights users on 12/3. 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.
Wed 12/313:03 pmSAN - ORD
Nonstop4h 27mAmerican Airlines
Wed 1/710:29 amORD - SAN
Nonstop4h 39mAmerican Airlines
Deal found 12/3$156
This United Airlines deal was found by Cheapflights users on 12/2. 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.
Tue 12/161:05 pmSAN - ORD
1 stop8h 05mUnited Airlines
Wed 1/147:10 amORD - SAN
Nonstop4h 30mUnited Airlines
Deal found 12/2$167
This Southwest deal was found by Cheapflights users on 12/3. 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.
Fri 12/266:35 amSAN - MDW
Nonstop4h 05mSouthwest
Tue 1/67:50 pmMDW - SAN
Nonstop4h 30mSouthwest
Deal found 12/3$168
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:25 amSAN - ORD
1 stop15h 47mMultiple Airlines
Wed 1/77:57 pmORD - SAN
1 stop19h 32mMultiple Airlines
Deal found 12/3$170
This Alaska Airlines deal was found by Cheapflights users on 12/3. 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.
Wed 12/178:00 amSAN - ORD
Nonstop4h 09mAlaska Airlines
Sat 1/173:44 pmORD - SAN
Nonstop4h 42mAlaska Airlines
Deal found 12/3$173
This Alaska Airlines deal was found by Cheapflights users on 12/3. 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.
Mon 12/295:31 pmSAN - ORD
Nonstop4h 28mAlaska Airlines
Mon 1/58:39 amORD - SAN
Nonstop4h 48mAlaska Airlines
Deal found 12/3$177
This United Airlines deal was found by Cheapflights users on 12/3. 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 12/1710:52 amSAN - ORD
Nonstop4h 11mUnited Airlines
Sat 1/172:40 pmORD - SAN
1 stop8h 09mUnited Airlines
Deal found 12/3$179
This Alaska Airlines deal was found by Cheapflights users on 12/2. 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.
Tue 12/301:30 pmSAN - ORD
Nonstop4h 32mAlaska Airlines
Tue 1/63:37 pmORD - SAN
Nonstop4h 42mAlaska Airlines
Deal found 12/2$184
This Alaska Airlines deal was found by Cheapflights users on 12/2. 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.
Tue 12/235:31 pmSAN - ORD
Nonstop4h 28mAlaska Airlines
Sun 1/48:58 pmORD - SAN
Nonstop4h 46mAlaska Airlines
Deal found 12/2$187
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:25 amSAN - ORD
2 stops29h 52mFrontier
Sat 1/176:02 pmORD - SAN
1 stop18h 06mFrontier
Deal found 12/3$188
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:25 amSAN - ORD
1 stop15h 47mFrontier
Sun 1/45:08 pmORD - SAN
1 stop22h 07mFrontier
Deal found 12/2$190
This Expedia deal was found by Cheapflights users on 12/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:25 amSAN - ORD
1 stop13h 02mMultiple Airlines
Tue 1/68:58 pmORD - SAN
Nonstop4h 46mMultiple Airlines
Deal found 12/2$193

Find 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 December 4, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$155
(United Airlines)

One-way from

$88
(Kiwi.com)

Popular in

April

Cheapest in

October

Average price

$321

Good round-trip deal

$258 or less

Good one-way deal

$128 or less
Provider with most accurate pricing for San Diego-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for San Diego-Chicago (CHI) flights.
From San Diego to Chicago (CHI)
One-way flight from San Diego to Chicago (CHI)
Highest demand for flights based on searches. 18% potential increase in price ($71 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in December 2025
Price to beat on a round-trip flight from San Diego to Chicago (CHI).
Price to beat on a one-way flight from San Diego to Chicago (CHI).

Cheapflights Fare Finder

 
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 December 4, 2025.
Use the filters below to find and compare flights from San Diego to Chicago that are best for you.

Fly from

San Diego

Fly to

Chicago

Route

Depart

Return

Price

San DiegoChicago

SAN - ORD

SANORD

San Diego

Tue 3/10

8:35 am-2:58 pm

Nonstop4h 23m

Chicago O'Hare Intl

Wed 3/11

3:07 pm-5:52 pm

Nonstop4h 45m

$157

San DiegoChicago

SAN - ORD

SANORD

San Diego

Tue 3/3

8:35 am-2:58 pm

Nonstop4h 23m

Chicago O'Hare Intl

Tue 3/10

7:00 am-3:46 pm

1 stop10h 46m

$164

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 1/8

7:35 am-5:15 pm

1 stop7h 40m

Chicago Midway

Wed 1/14

7:50 pm-10:20 pm

Nonstop4h 30m

$165

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sun 2/8

5:10 pm-11:37 pm

Nonstop4h 27m

Chicago O'Hare Intl

Sun 2/15

3:07 pm-5:52 pm

Nonstop4h 45m

$165

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sun 3/8

5:42 pm-11:59 pm

Nonstop4h 17m

Chicago O'Hare Intl

Wed 3/11

7:40 am-10:29 am

Nonstop4h 49m

$167

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sun 3/1

5:42 pm-11:59 pm

Nonstop4h 17m

Chicago O'Hare Intl

Sat 3/7

8:20 am-11:09 am

Nonstop4h 49m

$167

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Mon 2/2

7:20 am-4:30 pm

1 stop7h 10m

Chicago Midway

Fri 2/6

8:35 pm-11:05 pm

Nonstop4h 30m

$172

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Thu 1/15

6:30 pm-12:25 am

Nonstop3h 55m

Chicago Midway

Mon 1/19

8:00 am-10:35 am

Nonstop4h 35m

$175

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 2/13

5:42 pm-11:59 pm

Nonstop4h 17m

Chicago O'Hare Intl

Mon 2/16

8:20 am-11:09 am

Nonstop4h 49m

$177

San DiegoChicago

SAN - ORD

SANORD

San Diego

Mon 12/29

5:31 pm-11:59 pm

Nonstop4h 28m

Chicago O'Hare Intl

Mon 1/5

8:39 am-11:27 am

Nonstop4h 48m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 54 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on San Diego-Chicago flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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.

Cheapflights Insights

Everything you need to know about your flight from San Diego to Chicago

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 November 28, 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 44 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, February is the cheapest month in which you can book a flight from San Diego to Chicago (average of $95). Flying from San Diego to Chicago in May is currently the most expensive (average of $175). 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 December 4, 2025.

It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 30% 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 November 29, 2025.

Travelers seeking maximum savings on their San Diego to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday at noon 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 December 4, 2025.

The most flights from SAN to CHI are scheduled on a Wednesday (40 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 on average).

How often are flights from San Diego to Chicago delayed?

About 9% of weekly flights between San Diego and Chicago have experienced delays in the past year, with the average delay time being 171 minutes.

What is the most punctual flight time for San Diego to Chicago flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Monday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on San Diego to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 7% of flights being delayed.

The best insider tips for San Diego to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your San Diego to Chicago trip
Airports
SAN

Plan to arrive at least two hours before your flight from SAN to avoid stress, especially during peak traffic times.

ORD

Use the 'L' train for a reliable and quick way to reach downtown Chicago from ORD, avoiding traffic delays.

Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Blane Bachelor

Blane Bachelor

Expert on SAN

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more

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 December 4, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and United Airlines from San Diego to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.

Boarding

8.1

Entertainment

7.0

Food

7.1

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.

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 34 flights from San Diego to Chicago per day from 8 different airlines.

  • How long is the flight from San Diego to Chicago?

    Airlines like Alaska Airlines and Southwest fly from San Diego to Chicago in about 4h 23m. The time it takes to get you to your destination can typically vary by up to 3h 17m. Airlines will cover a distance of 1719 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Spirit Airlines, at $98, was found to be the cheapest airline from San Diego to Chicago.Alternate airlines to your destination round-trip include Frontier and Alaska Airlines. You may be able to fly from San Diego to Chicago for 69% 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 $45 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $61 and Southwest from $62 one-way.

  • What are the most popular routes 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: Cathay Pacific (93%), Austrian Airlines (89%), Aer Lingus (86%).

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

    On average you can expect to pay $838 for a flight from San Diego to Chicago. The cheapest flight overall is $78 while the most popular route, (San Diego - Chicago O'Hare Intl) is currently priced at $90.

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

  • 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, Fountains of Bellagio, and Stratosphere Tower. Fremont Street Experience, Fountains of Bellagio, and Stratosphere Tower can be accessed by traveling approximately 5.9 mi, 2.3 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.

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

  • 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, February is the cheapest month in which you can book a flight from San Diego to Chicago (average of $95). Flying from San Diego to Chicago in May is currently the most expensive (average of $175). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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.

Top 8 airlines flying from San Diego to Chicago

Discover the top 8 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$99Average$182FlexibilityNo cancel feeOn-time65%
FrontierCheapest$110Average$214FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$139Average$197FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$139Average$260FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$166Average$359FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$191Average$397FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$205Average$393FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$354FlexibilityNo cancel feeOn-timeN/A

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