$67 Find Cheap Flights from San Diego to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Diego to Illinois departing on 2/26. 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 Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Diego to Illinois.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Diego to Illinois.
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Cheap Flights from San Diego to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicagononstop$157
Moline
Moline1 stop$334
Peoria
Peoria1 stop$399
Bloomington
Bloomington1 stop$527
St. Louis
St. Louis1 stop$162
Chicago
Chicagononstop$157
Moline
Moline1 stop$334
Peoria
Peoria1 stop$399
Bloomington
Bloomington1 stop$527
St. Louis
St. Louis1 stop$162

Book Cheap San Diego to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Diego to Illinois 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 San Diego to Illinois

Wed, Mar 4 - Wed, Mar 18
Alaska Airlines Logo
8:35 am - 2:58 pm
SAN
-
ORD
4h 23mnonstop
Alaska Airlines Logo
4:10 pm - 6:55 pm
ORD
-
SAN
4h 45mnonstop
$157Alaska Airlines
Mon, Feb 23 - Tue, Feb 24
Frontier Logo
9:50 am - 10:30 pm
SAN
-
ORD
10h 40m
1 stop
Frontier Logo
9:05 am - 8:24 pm
ORD
-
SAN
13h 19m
1 stop
$158Frontier
Wed, Feb 18 - Fri, Feb 20
Frontier Logo
9:45 am - 10:26 am
SAN
-
ORD
22h 41m
1 stop
Frontier Logo
9:17 pm - 7:53 pm
ORD
-
SAN
24h 36m
1 stop
$162Frontier
Thu, Apr 9 - Sat, Apr 18
American Airlines Logo
3:07 pm - 9:28 pm
SAN
-
ORD
4h 21mnonstop
American Airlines Logo
8:45 pm - 11:16 pm
ORD
-
SAN
4h 31mnonstop
$165American Airlines
Wed, Apr 22 - Sun, Apr 26
United Airlines Logo
2:05 pm - 8:17 pm
SAN
-
ORD
4h 12mnonstop
United Airlines Logo
7:00 am - 9:40 am
ORD
-
SAN
4h 40mnonstop
$167United Airlines
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
5:55 pm - 11:45 pm
SAN
-
MDW
3h 50mnonstop
Southwest Logo
8:55 pm - 11:25 pm
MDW
-
SAN
4h 30mnonstop
$167Southwest
Fri, May 15 - Wed, May 20
American Airlines Logo
3:07 pm - 9:28 pm
SAN
-
ORD
4h 21mnonstop
American Airlines Logo
8:45 pm - 11:16 pm
ORD
-
SAN
4h 31mnonstop
$168American Airlines
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
9:20 am - 5:10 pm
SAN
-
MDW
5h 50m
1 stop
Southwest Logo
6:20 pm - 10:35 pm
MDW
-
SAN
6h 15m
1 stop
$168Southwest
Sat, Feb 14 - Sat, Feb 21
Hawaiian Airlines Logo
8:35 am - 2:58 pm
SAN
-
ORD
4h 23mnonstop
Hawaiian Airlines Logo
3:07 pm - 5:52 pm
ORD
-
SAN
4h 45mnonstop
$170Hawaiian Airlines
Fri, Apr 17 - Mon, Apr 20
United Airlines Logo
2:05 pm - 11:57 pm
SAN
-
PIA
7h 52m
1 stop
United Airlines Logo
5:25 pm - 10:59 pm
PIA
-
SAN
7h 34m
1 stop
$399United Airlines
Booking Insights

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

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

What is the cheapest San Diego to Illinois flight route?

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

The cheapest ticket to Illinois from San Diego found in the last 72 hours was to Chicago, at $157 round-trip. The most popular route is from San Diego (SAN) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $157.

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

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.

No, with an average price for the route of $274, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Diego to Illinois, 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 San Diego to Illinois is October, when tickets cost $237 (return) on average. On the other hand, the most expensive months are April and May, when the average cost of round-trip tickets is $386 and $377 respectively.

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

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

When flying from San Diego to Illinois, you should consider leaving on a Thursday and avoid Sundays if you are looking for the best rates. For your return to San Diego, you’ll find the best rates on Saturdays and the most expensive ones on Mondays.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from San Diego to Illinois, 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 San Diego to Illinois, you should book around 3 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$67
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from San Diego to St. Louis

FAQs - booking Illinois flights

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

    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 San Diego to Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Diego to Illinois 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 San Diego to Illinois?

    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 from San Diego to Illinois with an airline and back with another airline.

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

    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 from San Diego to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $262 on average. Morning departures are around 72% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the morning, which is peak travel time and where the average cost of a ticket is $451.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from San Diego to the following destinations at these prices or less: Chicago $140 one-way - $248 round-trip

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

 
See real verified KAYAK customer reviews for airlines flying from San Diego to Illinois. 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 San Diego to Illinois? 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.
8.0
Alaska AirlinesOverall score based on 11825 reviews
8.5Crew
8.1Boarding
7.0Entertainment
7.8Comfort
7.1Food
Airline reviews

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

4.0 OkayJerry, Jan 2026
SAN - ORD
Read more Alaska Airlines reviews

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

Again, very smooth and all of the Alaska folks were great. They continue to meet all my needs.

The whole experience went smoothly with no hitches along the way.

My Alaska Airlines return flight, although worked out in the end, didn't start off well. The initial plane that my family and I boarded was grounded because of a mishap that happened to one of the engines and everyone on board had to disembark the plane. Thankfully we were accommodated with a another plane but our initial flight was supposed to have departed at 11 pm San Diego time for Orlando but instead we ended up leaving at 1:40 am San Diego time. All Passengers were informed that part of the delay was that the plane had to be inspected by the captain, the food had to be stocked and the individuals responsible for fueling the plane left for the evening and had to be summoned to return to fill up our. The Alaska Airlines crew at the airport and on the plane were awesome and apologetic. I know that the crew wasn't responsible for the mishap of the engine but I think in the future the airline should offer a complimentary drink or (1) item of food other than pretzels, nuts or chips to all passengers since we're not to blame for the extreme set backs. The airline in general is good and I recommend to all flyers.

Late leaving so threatened our connection in Vegas to Seattle. We did make up time and made our connection.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

Was late but $50 voucher was great benefit of the summit card.

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

I truly appreciated the kindness and attentiveness of the staff and flight attendants. They did their best to be prompt with departure times to San Diego and back to New York! Alaska Airlines ... you are awesome!!

I've never flied them before but liked them. Weather was bad so a little scarey but they did a great job landing.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

The seats were comfortable, and the boarding process was pretty smooth.

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

We got exit row seats both flights. Everything was running on time

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

The food was terrible this time. Otherwise pleasant, quiet, on-time.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

We were delayed three times ,and that destroyed my plans, and reservations

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

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

Information on your arrival and departure airports