Cheap flights from San Diego to Chicago from $81
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Diego to Chicago departing on 9/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from San Diego to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Frontier flights from San Diego to Chicago Midway Airport
Our best Frontier deals on San Diego to Chicago Midway Airport flight tickets
Southwest flights from San Diego to Chicago Midway Airport
Our best Southwest deals on San Diego to Chicago Midway Airport flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from San Diego to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago Midway Airport?
The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from San Diego, with most prices found around $296. If you are unable to visit Chicago Midway Airport during the month of December, then departing from San Diego during the month April is also very affordable. Most momondo users find prices during this month for around $318.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from San Diego. The lowest ticket price found for a Wednesday departure recently was $421. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from San Diego because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $560.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from San Diego in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $397 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $545. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest San Diego to Chicago Midway flight route?
Fly from San Diego to Chicago Midway for the best San Diego - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from San Diego when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $360 when searching 16 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from San Diego for as low as $287 on momondo.
What cabin class options are available on San Diego to Chicago Midway flights?
There are 1 cabin classes available to choose from on San Diego to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from San Diego to Chicago Midway?
Southwest, Frontier, and Delta are the most popular carriers operating from San Diego to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from San Diego according to our data. Southwest is the first choice among our users, with 61% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from San Diego to Chicago Midway Airport on average per day?
As of June 2025, there are 2 flights per day flying from San Diego to Chicago Midway Airport. The most common time of day flights depart is 5:00PM, with 66% of flights taking off at noon.
How many flights depart from San Diego to Chicago Midway Airport on average per week?
As of June 2025, there are 18 flights per week flying from San Diego to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 22% of flights taking off on this day.
When to book flights from San Diego to Chicago Midway Airport
Cheap San Diego to Chicago Midway Airport (SAN to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from San Diego to Chicago Midway Airport
How far is San Diego to Chicago Midway by plane?
A flight from San Diego to Chicago Midway will travel around 1723.1 mi. Flights usually cover this in 3h 55m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from San Diego Airport to Chicago Midway Airport?
Prices for flights from San Diego Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from San Diego Airport to Chicago Midway Airport?
As of June 2025, there are 3 operators available to choose from for flights from San Diego Airport to Chicago Midway Airport.
How old do you have to be to fly from San Diego Airport to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Diego Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from San Diego to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from San Diego to Chicago Midway Airport is Boeing 737-800, representing 27.06% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 14.04%, Airbus A321neo at 12.41%, and Airbus A321-100/200 at 12.24%.
What is the most popular airline from San Diego to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from San Diego to Chicago Midway Airport is Southwest (57% of total bookings). The next most popular airlines are Frontier (37%) and Delta (5%).
Best airlines flying from San Diego to Chicago Midway Airport
Compare and see reviews for airlines that fly from San Diego to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $121 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $258 | Free Cancellation | Rating 8.0 7,950 reviews | |||
| PriceFrom $306 | Free Cancellation | Rating 8.0 4,287 reviews |
Southwest Flights From San Diego to Chicago Midway Airport
The lowest priced Southwest flight from San Diego to Chicago Midway Airport from the last 72 hours was $306. Generally, Southwest has 18 flights on this route every week with an average price of $457. Southwest is rated 8.0/10 by our users.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from San Diego to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San Diego to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from San Diego to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from San Diego on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from San Diego to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from San Diego. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from San Diego to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from San Diego are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.