CHI - SAN

$149 Find Cheap Flights from Chicago to San Diego

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San Diego departing on 8/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to San Diego

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Diego.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Diego.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$293
Typical prices: $278-$402
Southwest
Wed 8/26Tue 9/1
MDW - SAN • 1 stop
Cheapest non-stop
$297
Typical prices: $258-$497
Southwest
Thu 8/27Mon 8/31
MDW - SAN • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds up to six inches more legroom on this route.
American Main Cabin Extra adds early boarding; MDW offers shorter security lines.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $293 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Alaska Airlines, American Airlines and others. Average duration is 4h 22m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 5% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $186 (round-trip)
Shortest trip • 6h 01m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 36% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 28% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
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)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to San Diego that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to San Diego

Wed, Aug 26 - Tue, Sep 1
Southwest Logo
2:05 pm - 6:20 pm
MDW
-
SAN
6h 15m
1 stop
Southwest Logo
9:35 am - 7:15 pm
SAN
-
MDW
7h 40m
2 stops
$293Southwest
Wed, Jul 15 - Tue, Jul 28
Frontier Logo
9:57 pm - 9:05 am
ORD
-
SAN
13h 08m
1 stop
Frontier Logo
4:12 pm - 5:37 am
SAN
-
ORD
35h 25m
2 stops
$293Frontier
Fri, Aug 7 - Thu, Aug 13
Multiple Airlines Logo
7:59 pm - 10:33 pm
ORD
-
SAN
4h 34mnonstop
Multiple Airlines Logo
6:35 am - 4:00 pm
SAN
-
ORD
7h 25m
1 stop
$294Multiple Airlines
Wed, Jul 8 - Wed, Jul 15
Frontier Logo
9:57 pm - 9:05 am
ORD
-
SAN
13h 08m
1 stop
Frontier Logo
10:00 am - 8:52 pm
SAN
-
ORD
8h 52m
1 stop
$295Frontier
Sat, Jul 11 - Sat, Jul 18
Frontier Logo
9:57 pm - 9:05 am
ORD
-
SAN
13h 08m
1 stop
Frontier Logo
6:25 am - 8:52 pm
SAN
-
ORD
12h 27m
1 stop
$296Frontier
Wed, Aug 19 - Sun, Aug 23
Delta Logo
10:54 am - 5:05 pm
MDW
-
SAN
8h 11m
1 stop
Delta Logo
10:25 pm - 9:59 am
SAN
-
MDW
9h 34m
1 stop
$297Delta
Wed, Jul 15 - Sun, Jul 19
Multiple Airlines Logo
9:57 pm - 11:51 pm
ORD
-
SAN
27h 54m
1 stop
Multiple Airlines Logo
5:23 pm - 11:36 pm
SAN
-
ORD
4h 13mnonstop
$297Multiple Airlines
Thu, Jul 9 - Mon, Jul 13
Frontier Logo
9:57 pm - 9:05 am
ORD
-
SAN
13h 08m
1 stop
Frontier Logo
8:51 pm - 5:37 am
SAN
-
ORD
6h 46m
1 stop
$298Frontier
Wed, Jul 22 - Wed, Jul 29
Multiple Airlines Logo
7:15 am - 2:08 pm
ORD
-
SAN
8h 53m
1 stop
Multiple Airlines Logo
5:23 pm - 11:36 pm
SAN
-
ORD
4h 13mnonstop
$299Multiple Airlines
Wed, Aug 19 - Tue, Aug 25
Southwest Logo
10:30 am - 3:25 pm
MDW
-
SAN
6h 55m
2 stops
Southwest Logo
9:05 am - 5:25 pm
SAN
-
MDW
6h 20m
1 stop
$302Southwest
Booking Insights

KAYAK's insights & trends for Chicago to San Diego flights

Get data-powered insights and trends into flights from Chicago to San Diego to help you find the cheapest flights, the best time to fly and much more.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to San Diego departing in August.

What is the cheapest Chicago to San Diego flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to San Diego costs $298 on the route between Chicago O'Hare Intl Airport (ORD) and San Diego (SAN). Over the past month, this route was, on average, 5% cheaper than other Chicago-San Diego routes. It is also the most popular route.

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

The average price of all round-trip flights from Chicago to San Diego clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to San Diego, look for departures on Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from San Diego, Friday is the cheapest day to fly and Sunday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to San Diego, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to San Diego is February, where tickets cost $226 (return) on average. On the other hand, the most expensive months are March and May, where the average cost of round-trip tickets is $408 and $358 respectively.

Can I save money by flying with a layover from Chicago to San Diego?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $364 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to San Diego, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to San Diego, you should book around 3 weeks before departure, which saves you about 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to San Diego

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
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.

Good to know

Low seasonSeptember
Cheapest flight$149
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 21% 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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to San Diego

  • 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.

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

    In the last 5 days, the lowest price for a flight from Chicago to San Diego was $149 for a one-way ticket and $293 for a round-trip.

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

    No, a passport isn't needed to fly from Chicago to San Diego. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to San Diego?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. San Diego is the only airport in San Diego. You’ll usually find the cheapest deals if you fly from Chicago Midway Airport.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to San Diego?

    American Airlines, Alaska Airlines, JetBlue, and Hawaiian Airlines offer inflight Wi-Fi service on the Chicago to San Diego flight route.

  • Which aircraft models fly most regularly from Chicago to San Diego?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to San Diego flight route.

  • Which airline alliances offer flights from Chicago to San Diego?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and San Diego, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Chicago to San Diego?

    There are nonstop flights from Chicago to San Diego on a daily basis.

  • Which is the best airline for flights from Chicago to San Diego, Alaska Airlines or Southwest?

    The two airlines most popular with KAYAK users for flights from Chicago to San Diego are Alaska Airlines and Southwest. With an average price for the route of $313 and an overall rating of 7.9, Alaska Airlines is the most popular choice. Southwest is also a great choice for the route, with an average price of $311 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Chicago to San Diego?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to San Diego.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to San Diego?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Diego from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to San Diego?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Diego with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to San Diego?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Diego from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to San Diego

  • Looking for a cheap flight? 25% of our users found flights on this route for $178 or less one-way and $359 or less round-trip.
  • 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?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying 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

Reviews of the top 5 airlines serving from Chicago to San Diego

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Diego. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to San Diego? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
Alaska AirlinesOverall score based on 12577 reviews
8.5Crew
7.0Entertainment
7.0Food
8.1Boarding
7.8Comfort
Airline reviews

The flight was on time, seats were comfortable, crew is friendly and professional. Nice flight overall. Thanks!

10.0 ExcellentElena, Jun 2026
DFW - SAN
Read more Alaska Airlines reviews

The flight was on time, seats were comfortable, crew is friendly and professional. Nice flight overall. Thanks!

The plane was delayed almost 3 hours. I had a first class seat and there was no food loaded due to the late night departure (no nuts, not meal and no cookie), and the first class bathroom was out of order. Truly a disappointment all around.

Over all it was great. My original flight was canceled but they quickly rebooked me. I was frustrated because I had to cancel my entire plans for the day but all considered, not bad. The crew tried to keep us calm while we sat in the plane for was felt was an hour or so but they could use a bit of a script. The seats were comfortable and I would give it another try.

Having the internet available while flying was great. Better than having to choose from watching movies from a limited selection.

Not able to get boarding pass for domestic connection flight when check in at international airport. I was told I need to get connection flight boarding pass after I entered US. It us very inconvenient.

I was very impressed at how Alaska Airlines handles people with medical needs.

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

My flight got canceled never left san diego and miss out my fam event

3 hour delay. Had to change plans and was still delayed.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Our first flight was so delayed that we had 10 mins to board the next one. We requested if the flight attendant could allow us off there plane first and they denied our request even though I have seen this done before. Luck was on our side that we didn’t miss our next flight.

Everything was great except for the in-flight wifi that wasn't working.

It was great! The new boeing has much more space and charging ports!

Took a little longer than normal, but the process is clear and easy to understand.

Baggage check in would have been better if the service clerk told the other clerk that she was merging her two long lines of customers with her line so she could move luggage. Instead she only told the customers. When I told the agent and ask if she could direct who is next in line so we weren’t trying to cut in front of each other she said it’s not her problem and she can’t work three lines. I was shocked. Understood that they were working more than their share but some organization so the customers aren’t getting upset at each other would have gone a long way

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Terrible, if possible won't be flying again anytime soon!

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Connecting flights were poor,especially in Naples.our Lufthansa air bus was a joke.way too small for that long of a flight.no room at all.couldn’t even get out of the seats to move around or go to the bathrooms.we thought we were getting an actual air bus,double decker.i will never fly that long in a plane like that again.kind of misleading to call it an air bus.we actually had more room on our buses that we used.

For a 22 minute flight all you expect is for it to be safe and comfortable

Lost connnection had to stayON in Chicago Was a mess

Booked economy through United - air canada treated it as standby and was almost refused boarding.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

We are too tired and frustrated to comment politely at this point

My flight was delayed for several hours. Sitting at gate 16 for several hours, I got a text from Kayak the gate changed to 9 before it was announced. Very bad communication at each gate from American Airlines employees. I received 10 notifications of delay from Kayak. My vacation started off horrible! I will write to American Airlines corporate office also.

The service and food needs to improve to catch up with other international flights

The flight crew was fantastic! Which the seats had a small TV.

also wi-fi never worked attendant said satellite coverage is spotty over water ..... but we were over land!

They attended to my needs as I couldn't walk and they provided a wheelchair for me.q

This time my flight was smooth and uneventful. They started boarding even earlier than it was scheduled. I was pleasantly surprised. Thank you!

Boarding was a mess - the agent basically called every group in rapid succession, so there was no organization at all. The economy seats are a joke, and main cabin extra seats were sold out when I purchased my flight. As such, I was locked in the same position for four hours. Being 6’6”, it was impossible to get my bag out from under the seat in front of me, and I couldn’t have used my laptop even if my bag were accessible due to the minuscule seat pitch. Also the wifi was broken. American is a joke - can’t wait until they merge with Spirit.

Cons: "Just seemed chaotic. Plane super late departing. Baggage pick up was a nightmare."

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

i was unable to check in the flight. refund requested

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

I went to the Frontier counter in San Jose at 1030am or so on Sunday 10/13/24 to see if I could get an earlier flight to San Diego in lieu of my reserved 630pm flight. One thing led to another, and I was able to obtain an open seat for about $ 56. on the earlier flight. Fine. Then the agent asked if I "was checking a bag". Not knowing that carry-ons cost extra per Frontier policy, I thought that she meant a regular checked bag. Therefore, I said no. Once I got to the gate, the same gate agent who sold me a ticket told me that I had to pay $99 for a carry-on, and that all bags were extra on Frontier. Having never flown on Frontier, I was not aware of this. Part of the issue was that she was not a native English speaker, so there was a miscommunication as to what "bag" meant. I would have preferred for her to have clearly let me know at the front counter that any bag including a carry-on cost $99. It would have had the same outcome, as I had to take my carry-on. But it got hectic at the last minute at the gate itself. The baggage policy should have mentioned "including carry-ons" when we first spoke.

Literally everything could have been better. Why are the planes always late?

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

The boarding time. I was in Section 1 the lady in charge just let people in section 3 without see us. Make a line , I have to step out and ask her. We were in the line and she just take my ticket and that’s it, so if I don’t ask her she could leave us at the end! We paid more for that privilege and. She doesn’t care….

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

Other airlines flying from Chicago to San Diego

Flights from the other most popular airlines that fly from Chicago to San Diego according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.