CHI - SAN

$124 Find Cheap Flights from Chicago to San Diego - Compare and Save

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Everything you should know

Cheapest round-trip
$249
Typical prices: $226-$398
Frontier
Mon 10/22Fri 10/26
ORD - SAN • 1 stop
Cheapest non-stop
$252
Typical prices: $225-$399
Alaska Airlines
Fri 10/5Thu 10/11
ORD - SAN • Non-stop
Nonstop flights
You can fly direct with American Airlines, United Airlines and others. Average duration is 4h 28m.
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 13% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 46% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $193 (round-trip)
Shortest trip • 6h 24m (one-way)
Insights
Insights
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We hope you love your trip to San Diego!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to San Diego

Thu, Oct 22 - Mon, Oct 26
Frontier Logo
6:30 am - 11:56 pmORD  Chicago O'Hare Intl-SAN San Diego
19h 26m1 stop Denver Intl
Frontier Logo
6:25 am - 10:01 amSAN  San Diego-ORD Chicago O'Hare Intl
25h 36m1 stop Denver Intl
$249Frontier
Fri, Oct 2 - Fri, Oct 9
Frontier Logo
1:01 pm - 12:53 pmORD  Chicago O'Hare Intl-SAN San Diego
25h 52m2 stops Dallas/Fort Worth Phoenix Sky Harbor Intl
Frontier Logo
8:34 pm - 5:16 amSAN  San Diego-ORD Chicago O'Hare Intl
6h 42m1 stop Las Vegas Harry Reid Intl
$249Frontier
Wed, Oct 21 - Sun, Oct 25
Multiple Airlines Logo
2:21 pm - 5:01 pmORD  Chicago O'Hare Intl-SAN San Diego
4h 40mnonstop
Multiple Airlines Logo
6:25 am - 12:24 amSAN  San Diego-ORD Chicago O'Hare Intl
15h 59m1 stop Denver Intl
$249Multiple Airlines
Sat, Oct 17 - Tue, Oct 20
Multiple Airlines Logo
6:30 am - 3:58 pmORD  Chicago O'Hare Intl-SAN San Diego
11h 28m1 stop Denver Intl
Multiple Airlines Logo
12:35 pm - 6:53 pmSAN  San Diego-ORD Chicago O'Hare Intl
4h 18mnonstop
$249Multiple Airlines
Mon, Oct 5 - Sun, Oct 11
Alaska Airlines Logo
7:49 pm - 10:27 pmORD  Chicago O'Hare Intl-SAN San Diego
4h 38mnonstop
Alaska Airlines Logo
5:46 pm - 11:59 pmSAN  San Diego-ORD Chicago O'Hare Intl
4h 13mnonstop
$252Alaska Airlines
Wed, Oct 7 - Mon, Oct 12
American Airlines Logo
9:00 pm - 11:33 pmORD  Chicago O'Hare Intl-SAN San Diego
4h 33mnonstop
American Airlines Logo
10:40 pm - 4:49 amSAN  San Diego-ORD Chicago O'Hare Intl
4h 09mnonstop
$252American Airlines
Tue, Oct 13 - Tue, Oct 20
Alaska Airlines Logo
7:20 am - 9:56 amORD  Chicago O'Hare Intl-SAN San Diego
4h 36mnonstop
Alaska Airlines Logo
7:00 am - 1:25 pmSAN  San Diego-ORD Chicago O'Hare Intl
4h 25mnonstop
$253Alaska Airlines
Wed, Sep 16 - Sat, Sep 19
Southwest Logo
2:05 pm - 6:20 pmMDW  Chicago Midway-SAN San Diego
6h 15m1 stop Houston Hobby
Southwest Logo
10:40 pm - 4:30 amSAN  San Diego-MDW Chicago Midway
3h 50mnonstop
$253Southwest
Wed, Oct 28 - Mon, Nov 2
Southwest Logo
6:55 am - 10:45 amMDW  Chicago Midway-SAN San Diego
5h 50m1 stop Phoenix Sky Harbor Intl
Southwest Logo
10:40 pm - 4:25 amSAN  San Diego-MDW Chicago Midway
3h 45mnonstop
$253Southwest
Fri, Sep 11 - Tue, Sep 15
American Airlines Logo
9:05 pm - 11:25 pmORD  Chicago O'Hare Intl-SAN San Diego
4h 20mnonstop
American Airlines Logo
7:32 am - 1:59 pmSAN  San Diego-ORD Chicago O'Hare Intl
4h 27mnonstop
$259American Airlines
Booking Insights

Price, demand and travel trends for Chicago to San Diego flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago to San Diego with more confidence.

How much is a round-trip flight from Chicago to San Diego?

Round-trip flights from Chicago to San Diego start at $249. Prices are typical for this route right now, with typical round-trip fares ranging from $226 to $398. The lowest price found in the past 5 days was $249 on Frontier.

What is the cheapest Chicago to San Diego flight route?

Chicago O'Hare Intl Airport (ORD) to San Diego (SAN) is the cheapest Chicago to San Diego route, averaging $313 round-trip. Other Chicago to San Diego routes average $383, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Chicago to San Diego?

Wednesday is the cheapest day of the week to fly from Chicago to San Diego, it is 4% cheaper than the average day. Sunday is the most expensive day with flight prices 9% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • February is the cheapest month to fly from Chicago to San Diego at $243 round-trip.
  • July ($363) and June ($363) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 49% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Chicago to San Diego the cheapest?

Flights from Chicago to San Diego are cheapest 7 weeks before departure. Booking in this window typically costs about 46% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Chicago to San Diego

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

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.

Brandon Schultz

Brandon Schultz

Expert on SAN

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Key details for Chicago to San Diego flights

Low season

September

Cheapest flight

$124
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago Midway Airport to San Diego

When to book flights from Chicago to San Diego

Are your dates flexible? Find out the best times to travel from Chicago to San Diego based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago to San Diego flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Is there free Wi-Fi at O'Hare International Airport?

    Unlimited free Wi-Fi is available at the O'Hare International Airport throughout all terminals. If you want to access the Wi-Fi, enable wireless connection on your device and connect to “_Free_ORD _Wi-Fi” or “Boingo Hotspot.”

  • Are there nonstop flights from Chicago to San Diego?

    For flights from Chicago to San Diego, there are several airlines that serve this route, including American Airlines and United Airlines. Both offer nonstop flights from the O'Hare International Airport to the San Diego International Airport. You can also find flights by Frontier, which flies through Denver International Airport (DEN), but it could take longer, so book through KAYAK to compare routes and find the best option.

  • Where’s the chapel at O'Hare International Airport?

    The O'Hare International Airport offers a chapel, a peaceful space in the busy airport you can use for prayers, liturgies, and worship. It’s equipped with prayer books, worship materials, rosaries, rugs, and Juma ablution facilities. The facility is in Terminal 2 Mezzanine level above Delta Air ticket counters next to USO.

  • Are there lactation rooms at San Diego Airport?

    Mothers can access three lactation rooms found in each terminal post-security. In Terminal 1 West, you can find the lactation rooms on the second level. The rooms in Terminal 1 East are near the security checkpoint, while in Terminal 2 West, they’re on the second level. Each of these rooms is equipped with electrical outlets, artwork, a handwashing station, soft lighting, comfortable seating, and a children’s seat.

  • Are there hotels near the San Diego International Airport?

    There are no hotels within the airport. The closest near the airport is the Sheraton Hotel & Marina, located at a 10min walking distance or 3min if you’re using the free hotel shuttle. The Hampton Inn & Suites is located about a mile away, a 5min drive from the terminal. You can also book the TownPlace Suites by Marriott, located at a 5min driving distance from the airport.

  • Which airlines offer extra legroom and free seat selection on Chicago to San Diego flights?

    Among airlines operating Chicago to San Diego flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • Alaska Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Chicago to San Diego?

    4 airlines operate flights between Chicago and San Diego. The airlines offering nonstop flights on this route include:
    • American Airlines
    • United Airlines
    • Southwest
    • Alaska Airlines

  • Which airports can I use when flying from Chicago to San Diego?

    Flights from Chicago to San Diego may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at San Diego (SAN).

  • Which airlines include bags at no extra cost on Chicago to San Diego flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • Alaska Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Chicago to San Diego?

    Four cabin classes are available on flights from Chicago to San Diego:

    • Economy Class
    • Premium Economy Class
    • Business Class
    • First Class

    Prices vary by airline.

  • How much can I save by taking a layover when flying from Chicago to San Diego?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $193 round-trip via Minneapolis St Paul (MSP), compared to $315 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago to San Diego?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Chicago to San Diego pass through?

    One-stop flights from Chicago to San Diego most commonly connect through:

    • Denver Intl (DEN) - 30% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 27% of one-stop connections
    • Las Vegas Harry Reid Intl (LAS) - 11% of one-stop connections
    • Dallas/Fort Worth (DFW) - 10% of one-stop connections

    Denver Intl (DEN) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago to San Diego?

    Yes. Being flexible with your travel dates can save you up to 12% on the Chicago to San Diego route. Wednesday is the cheapest departure day at $304 round-trip on average, while Sunday is the most expensive at $343, a difference of $39. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How are flight departures from Chicago to San Diego spread across the day?

    Morning is the busiest departure period on Chicago to San Diego flights, with 47% of flights leaving in that window. Night departures account for 26%, afternoon flights for 14%, and evening flights for 13%.

  • What popular places can I visit in San Diego?

    Some of the most popular sights in San Diego are Gaslamp Quarter, San Diego Convention Center and SeaWorld San Diego. These are among the most viewed places in San Diego on KAYAK.

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

    A nonstop flight from Chicago to San Diego takes 4h 28m, covering 1,732 miles.

  • What are the earliest and latest flights from Chicago to San Diego?

    These are the earliest and latest flight times available from Chicago to San Diego:

    • Earliest: departs at 5:25 am and lands at 9:53 am
    • Latest: departs at 9:38 pm and lands at 2:06 am.

    The flight takes about 4h 28m.

  • How expensive are last-minute Chicago to San Diego flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 44% above the route average of $314. Book 7 weeks before departure for the lowest fares.

  • Do I need a passport to fly from Chicago to San Diego?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Chicago to San Diego changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $249 to $2,466. That means the highest observed fare was about 10x higher than the lowest one.

  • How are flight prices from Chicago to San Diego looking right now?

    One-way fares from Chicago to San Diego are currently lower than usual. Average one-way flight prices are about $135, which is 32% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Chicago to San Diego?

    Flying via Salt Lake City (SLC) gives the shortest average 1-stop total travel time at 6h 24m, compared with 6h 29m via Minneapolis St Paul (MSP) and 6h 31m via Phoenix Sky Harbor Intl (PHX).

  • What is the time difference between Chicago and San Diego?

    San Diego is 2 hours behind Chicago (Pacific Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at San Diego Airport (SAN)?

    San Diego Airport (SAN) hosts 5 major car rental companies, with daily rates starting from around $14 for economy cars. Top options include:
    · Dollar
    · Payless
    · Europcar
    · Thrifty
    · Fox

  • How much should I expect to pay for a Chicago to San Diego flight?

    Round-trip flights from Chicago to San Diego range from $226 to $398, with an average of $314 over the past 12 months. Anything below $226 counts as a good deal.

  • Which airlines offer Wi-Fi on Chicago to San Diego flights?

    Three airlines offer in-flight Wi-Fi on Chicago to San Diego flights:

    • • Alaska Airlines
    • • American Airlines
    • • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

Your guide to booking Chicago to San Diego flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Wednesday departure instead of Sunday. On this route, Wednesday flights average $304 - about $39 less than Sunday (11% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 7 weeks before you fly. On this route, that window historically saves about 46% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago to San Diego trip for February. Fares historically average $243 round-trip in that month - typically $120 less than the most expensive month, which is June (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Minneapolis St Paul Airport (MSP) can be cheaper than flying direct. The cheapest layover option averages $193 round-trip on this route - about $122 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to San Diego Airport.
    - Courtyard by Marriott San Diego Downtown Little Italy
    - Bay Club Hotel & Marina
    - Wyndham Garden San Diego near SeaWorld
  • Located 14 miles from the Loop Business District, the O'Hare International Airport is the ideal airport if you’re traveling from Chicago to San Diego, California.
  • If you need shower facilities at the O'Hare International Airport, they’re available at Concourse C. You can also access the VIP lounge if you’re a VIP member and need these services.
  • For mothers with small children, the O'Hare International Airport offers a Mother’s Room to help mothers nurse, use a breast pump, and care for young children. The rooms are in each terminal.
  • The O'Hare International Airport offers free unlimited Wi-Fi. You can connect to the Wi-Fi by searching “_Free_ORD _Wi-Fi.” It comes with ads, but you can also use a premium high-speed option for a fee.
  • For flights from the O'Hare International Airport to San Diego, you can use the San Diego International Airport (SAN), located 3 miles from downtown San Diego.
  • When you arrive at San Diego International Airport, you can explore the dining options at Terminal 1, including Banker’s Hill Bar & Market. On Terminal 2, there are options like the Artisan Market and Starbucks at Gate 37.
  • To access cash, you can use ATMs throughout the San Diego International Airport. In Terminal 1, they’re past the checkpoint near Gate 1, in the lobby opposite the food court, near Gate 5, and near Gate 13. The ATMs are also available in Terminal 2.
  • There are courtesy phones at San Diego International Airport throughout the terminals, which offer complimentary local calls. For long-distance calls, you can purchase phone cards at most retail concessions.

Prefer to fly direct from Chicago to San Diego?

 
Find which airlines fly direct from Chicago to San Diego Airport, which days they fly and book direct flights.

Direct departures

Chicago to San Diego

Monday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Tuesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Wednesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Thursday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Friday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Saturday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Sunday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

See more direct flights

Direct returns

San Diego to Chicago

Monday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Tuesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Wednesday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Thursday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Friday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Saturday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

Sunday

Alaska Airlines,American Airlines,Southwest, +1 more

Alaska Airlines,American Airlines, +2 more

See more direct flights

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

Other airlines flying from Chicago to San Diego