HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$85+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from San Diego to Chicago are usually found in September or August, booked 73 days in advance, depart on a Wednesday or Thursday and return on a Friday

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 November 5, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$158
(Expedia)

One-way from

$85
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$306

Good round-trip deal

$260 or less

Good one-way deal

$135 or less
Provider with most accurate pricing for San Diego-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Diego-Chicago (CHI) flights.
Search Deals
From San Diego to Chicago (CHI)
Search Deals
One-way flight from San Diego to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from San Diego to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from San Diego to Chicago (CHI).
Search Deals

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 November 5, 2025.

This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1110:57 amSAN - ORD
1 stop7h 46mMultiple Airlines
Mon 12/158:59 pmORD - SAN
Nonstop4h 28mMultiple Airlines
Deal found 11/3$159
This Southwest deal was found by Cheapflights users on 11/3. 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.
Tue 12/26:30 amSAN - MDW
Nonstop4h 05mSouthwest
Wed 12/35:15 pmMDW - SAN
1 stop5h 55mSouthwest
Deal found 11/3$160
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Sat 12/61:05 pmSAN - ORD
1 stop8h 05mUnited Airlines
Sat 1/107:10 amORD - SAN
Nonstop4h 30mUnited Airlines
Deal found 11/4$161
This Southwest deal was found by Cheapflights users on 11/4. 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.
Mon 12/811:20 amSAN - ORD
1 stop8h 30mSouthwest
Wed 12/107:15 amORD - SAN
1 stop8h 20mSouthwest
Deal found 11/4$162
This Southwest deal was found by Cheapflights users on 11/4. 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.
Mon 12/88:05 pmSAN - MDW
1 stop7h 00mSouthwest
Wed 12/105:15 pmMDW - SAN
1 stop5h 55mSouthwest
Deal found 11/4$162
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Fri 12/56:34 amSAN - ORD
1 stop15h 38mFrontier
Sun 12/147:00 amORD - SAN
1 stop14h 15mFrontier
Deal found 11/4$163
This Southwest deal was found by Cheapflights users on 11/3. 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.
Mon 11/243:35 pmSAN - MDW
1 stop6h 45mSouthwest
Thu 11/277:45 amMDW - SAN
Nonstop4h 25mSouthwest
Deal found 11/3$163
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Thu 12/43:47 pmSAN - ORD
1 stop17h 55mMultiple Airlines
Tue 12/97:41 pmORD - SAN
2 stops29h 05mMultiple Airlines
Deal found 11/4$164
This Alaska Airlines deal was found by Cheapflights users on 11/3. 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 12/38:00 amSAN - ORD
Nonstop4h 09mAlaska Airlines
Sun 12/148:59 pmORD - SAN
Nonstop4h 28mAlaska Airlines
Deal found 11/3$165
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:30 amSAN - MDW
Nonstop4h 05mSouthwest
Mon 12/88:35 pmMDW - SAN
Nonstop4h 25mSouthwest
Deal found 11/2$165
This Southwest deal was found by Cheapflights users on 11/5. 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.
Thu 12/42:50 pmSAN - ORD
1 stop5h 45mSouthwest
Tue 12/97:15 amORD - SAN
1 stop8h 20mSouthwest
Deal found 11/5$166
This Southwest deal was found by Cheapflights users on 11/4. 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.
Tue 12/22:05 pmSAN - MDW
1 stop6h 30mSouthwest
Mon 12/86:00 pmMDW - SAN
1 stop6h 25mSouthwest
Deal found 11/4$166

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 November 5, 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 3/3

7:50 pm-5:03 am

1 stop7h 13m

Chicago O'Hare Intl

Wed 3/4

1:01 pm-3:41 pm

Nonstop4h 40m

$163

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 12/3

5:53 pm-11:50 pm

Nonstop3h 57m

Chicago O'Hare Intl

Mon 12/8

8:55 am-11:22 am

Nonstop4h 27m

$165

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sat 12/13

2:16 pm-8:25 pm

Nonstop4h 09m

Chicago O'Hare Intl

Sun 12/14

7:10 am-9:40 am

Nonstop4h 30m

$165

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 1/16

8:45 pm-5:05 am

1 stop6h 20m

Chicago Midway

Mon 1/19

8:35 pm-11:05 pm

Nonstop4h 30m

$167

San DiegoChicago

SAN - ORD

SANORD

San Diego

Mon 3/2

5:00 pm-11:10 pm

Nonstop4h 10m

Chicago O'Hare Intl

Sat 3/7

9:00 am-11:25 am

Nonstop4h 25m

$167

San DiegoChicago

SAN - ORD

SANORD

San Diego

Sun 1/25

5:10 pm-11:37 pm

Nonstop4h 27m

Chicago O'Hare Intl

Sat 1/31

9:00 am-11:43 am

Nonstop4h 43m

$167

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Fri 12/12

6:35 am-12:40 pm

Nonstop4h 05m

Chicago Midway

Tue 12/16

5:15 pm-9:10 pm

1 stop5h 55m

$170

San DiegoChicago

SAN - ORD

SANORD

San Diego

Wed 12/3

1:15 pm-10:35 pm

1 stop7h 20m

Chicago O'Hare Intl

Wed 12/10

7:15 am-1:35 pm

1 stop8h 20m

$172

San DiegoChicago

SAN - MDW

SANMDW

San Diego

Sun 2/1

8:45 pm-5:05 am

1 stop6h 20m

Chicago Midway

Mon 2/9

8:05 am-12:50 pm

1 stop6h 45m

$172

San DiegoChicago

SAN - ORD

SANORD

San Diego

Fri 1/30

8:00 am-2:29 pm

Nonstop4h 29m

Chicago O'Hare Intl

Mon 2/2

3:49 pm-6:31 pm

Nonstop4h 42m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 58 results
1
2
3
...
6

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 November.
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
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust 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 October 31, 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 73 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 $93). Flying from San Diego to Chicago in May is currently the most expensive (average of $173). 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 November 5, 2025.

It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 34% on the cost of your flight, compared to a flight in the evening.

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 2, 2025.

Travelers seeking maximum savings on their San Diego to Chicago flight should consider departing on Sunday mornings 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 November 5, 2025.

The most flights from SAN to CHI are scheduled on a Monday (40 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 on average).

How much does it cost to fly round-trip from San Diego to Chicago?

The best insider tips for San Diego to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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.

Read more about SANby Blane Bachelor
ORD

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

Read more about ORDby Ramsey Qubein
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 November 5, 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.
Alaska Airlines
8.0
Very good
11,241 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
11,241 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,239 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
9,000 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
11,039 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Frontier
5.8
Fair
3,115 reviews
Alaska Airlines
8.0
Very good
11,241 reviews

Crew

8.5

Overall

8.0

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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

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

    Airlines like United Airlines, Alaska Airlines, and Southwest fly from San Diego to Chicago in about 3h 57m. The time it takes to get you to your destination can typically vary by up to 3h 16m. 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 $110, was found to be the cheapest airline from San Diego to Chicago.Alternate airlines to your destination round-trip include Frontier and Hawaiian Airlines. You may be able to fly from San Diego to Chicago for 67% 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 $86 on Southwest. Other airlines that offer cheap prices include Alaska Airlines from $89 and United Airlines from $89 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: Cathay Pacific (90%), Royal Jordanian (90%), Aer Lingus (87%).

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

    On average you can expect to pay $893 for a flight from San Diego to Chicago. The cheapest flight overall is $87 while the most popular route, (San Diego - Chicago O'Hare Intl) is currently priced at $137.

  • 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.

  • 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 $55 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 Denver 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, February is the cheapest month in which you can book a flight from San Diego to Chicago (average of $93). Flying from San Diego to Chicago in May is currently the most expensive (average of $173). 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
Hammond
Porter
Benton Harbor
Merrillville

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for San Diego to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
San Francisco to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
San Francisco to Midway flights
San Diego to O'Hare Intl flights
Los Angeles to Midway flights
San Jose to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Burbank to O'Hare Intl flights
Oakland to O'Hare Intl flights
Los Angeles to St. Louis flights
San Francisco to St. Louis flights
Ontario to Midway flights
Santa Ana to Midway flights
San Diego to Midway flights
Oakland to Midway flights
Reno to O'Hare Intl flights
Ontario to St. Louis flights
San Diego to St. Louis flights
Sacramento to Midway flights
Las Vegas to Midway flights
Palm Springs to O'Hare Intl flights
Burbank to Midway flights
Las Vegas to St. Louis flights
San Jose to Midway flights
Fresno to O'Hare Intl flights
Long Beach to O'Hare Intl flights
Santa Ana to St. Louis flights
San Jose to St. Louis flights
Burbank to St. Louis flights
San Luis Obispo to O'Hare Intl flights
Reno to Midway flights
Fresno to Midway flights
Monterey to O'Hare Intl flights
Los Angeles to Peoria flights
Sacramento to St. Louis flights
Oakland to St. Louis flights
San Francisco to Moline flights
Ontario to Peoria flights
Los Angeles to Rockford flights
Santa Ana to Peoria flights
Long Beach to St. Louis flights
Santa Rosa to O'Hare Intl flights
San Francisco to Rockford flights
Long Beach to Midway flights
Los Angeles to Moline flights
Santa Barbara to O'Hare Intl flights
Palm Springs to Midway flights

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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$110Average$206FlexibilityNo cancel feeOn-time65%
FrontierCheapest$119Average$212FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$139Average$197FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$139Average$262FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$168Average$367FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$200Average$419FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$213Average$401FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$368FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.