Question 1

How much does a flight from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?

Accepted Answer

You can find cheap one-way flights from $124 and cheap return flights from $210 San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights generally range between $131 and $1087, and roundtrip flights usually range from $259 to $2188. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.

*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.

Question 2

What is the cheapest month to fly from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

The cheapest month to fly from SAN to ORD is September when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.

Question 3

Which airlines fly direct from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

Choose from 5 airlines operating direct flights from SAN to ORD:

United operates around 36 direct flights from SAN to ORD every week
American Airlines operates around 32 direct flights from SAN to ORD every week
Hawaiian Airlines operates around 12 direct flights from SAN to ORD every week
Finnair operates around 7 direct flights from SAN to ORD every week
Qatar Airways operates around 7 direct flights from SAN to ORD every week

Question 4

What is the cheapest airline that flies from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

JetBlue Airways is one of the cheapest airlines offering connecting flights from San Diego, CA (SAN) to Chicago, IL (ORD), with round-trip tickets starting from around $263. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

*Prices based on flights available on Expedia in the last year.

Question 5

How do I find cheap flights from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

To find a cheap flight from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

Question 6

What is the best airline to fly with from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

The best airline to fly with from San Diego, CA (SAN) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, American Airlines offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. United offers the most daily flights from SAN to ORD, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.

Question 7

What is the best time to fly from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

Question 8

How many flights per day from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

There are approximately 10 nonstop flights per day from San Diego Intl. (SAN) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.

Question 9

What is the earliest flight from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

The earliest flight from San Diego International Airport (SAN) to O'Hare International Airport (ORD) usually departs at around 12:55 AM. This seasonal service is operated by American Airlines, giving you a great opportunity to arrive in Chicago early and make the most of your time there. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

Question 10

What are the most popular departure times for flights from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

The most popular departure times for flights from San Diego Intl. (SAN) to O'Hare Intl. (ORD) are in the early morning, from 6am to 9am. About 32% of passengers prefer this time window. Many major carriers, including Delta, Alaska Airlines, and American Airlines, offer flights during this window. This timing works well because it allows you to arrive in Chicago with a full day ahead of you.

Question 11

How long does it take to fly from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

Direct flights from SAN to ORD usually take about 4 hours 20 minutes, traveling roughly 1,721 miles. If you opt for a connecting flight, expect to add around 4 hours 40 minutes to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.

Question 12

Can you fly business or first class from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

Business class seats are offered on the SAN to ORD route with American Airlines.

First class cabins are available on:

Delta Air Lines
United Airlines
American Airlines
Hawaiian Airlines

Question 13

How much is a business class flight from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

A direct, return business class ticket from San Diego (SAN) to Chicago (ORD) typically costs between $1,312 - $1,882. A non-stop, one-way business class flight is usually around $613 - $885. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.

*Prices based on flights available on Expedia in the last year.

Question 14

How do I earn miles on a San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?

Accepted Answer

It's easy to earn miles on a San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Question 15

What airports do you fly into for Chicago from San Diego Intl. (SAN)?

Accepted Answer

From San Diego Intl. (SAN), you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD) in Chicago. Some flights may connect through major hubs like Harry Reid Intl. (LAS), Sky Harbor Intl. (PHX), Denver Intl. (DEN) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Question 16

Is it cheaper to buy a plane ticket from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?

Accepted Answer

Typically, booking a last minute flight from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Question 17

Is it cheaper to book a San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?

Accepted Answer

Securing a San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

Question 18

Can I cancel or change the date of my flight from San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.)?

Accepted Answer

If you booked your San Diego, CA (SAN-San Diego Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Origin airport	San Diego Intl.
Destination airport	O'Hare Intl.
Airlines serving	Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Sun Country Airlines, United
Roundtrip price	$210
Distance	1720 mi
Average flight time	6 hours 11 mins

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$124 Cheap Flights from San Diego (SAN) to Chicago (ORD)