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

Flights overview

Useful information for finding cheap flights from San Diego to Chicago and booking your next trip

Cheapest round-trip flights	$142	Frontier 1 stop 9 hr Sat, Feb 14 — Fri, Feb 20	The cheapest round-trip flight from San Diego to Chicago is currently $142
Cheapest one-way flight	$65	Frontier 1 stop 8 hr Thu, Jan 15	The cheapest one-way flight from San Diego to Chicago is currently $65
Cheapest nonstop flights	$153	Alaska Nonstop 5 hr Sat, Feb 14 — Fri, Feb 20	The cheapest nonstop round-trip flight from San Diego to Chicago is currently $153
Last-minute weekend getaway	$422	Frontier 1 stop 24 hr Fri, Nov 21 — Mon, Nov 24	The cheapest last-minute weekend getaway from San Diego to Chicago is currently $422
Cheapest business class flights	$727	Alaska Nonstop 5 hr Thu, Jan 29 — Fri, Feb 6	The cheapest business class round-trip flight from San Diego to Chicago is currently $727

Fastest flight	3 hr 50 min	The fastest nonstop flight from San Diego to Chicago takes 3 hr 50 min
Nonstop flights	Every day	There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from San Diego to Chicago is typically February. The most expensive month to fly is typically May.

February Cheapest	Typical prices: $120–205
May Most expensive	Typical prices: $180–260

Popular airlines from San Diego to Chicago

Southwest

Nonstop

from $165

Typical price: $225–520

21 weekly nonstop flights

SAN - MDW Every day

2587 weekly connecting flights

SAN - MDW, ORD Every day
United

Nonstop

from $153

Typical price: $195–485

34 weekly nonstop flights

SAN - ORD Every day

415 weekly connecting flights

SAN - ORD Every day
American

Nonstop

from $155

Typical price: $210–550

21 weekly nonstop flights

SAN - ORD Every day

305 weekly connecting flights

SAN - ORD Every day
Alaska

Nonstop

from $155

Typical price: $265–600

21 weekly nonstop flights

SAN - ORD Every day

30 weekly connecting flights

SAN - ORD Every day
Delta

from $237

Typical price: $265–660

369 weekly connecting flights

SAN - MDW, ORD Every day
Frontier

from $130

Typical price: $145–320

52 weekly connecting flights

SAN - MDW, ORD Every day

Popular airports near San Diego

San Diego International Airport (SAN)

San Diego United States 10 min 2 mi
Tijuana International Airport (TIJ)

Tijuana Mexico 37 min 16 mi
Los Angeles International Airport (LAX)

Los Angeles United States 2 hr 2 min 111 mi
John Wayne Airport (SNA)

Santa Ana United States 1 hr 22 min 78 mi

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 31 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 26 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 28 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from San Diego to Chicago

When are the cheapest days to fly from San Diego to Chicago?

The cheapest flights from San Diego to Chicago are usually in February. Typical ticket prices in February range from $120 to $205.

Which airlines provide the cheapest flights from San Diego to Chicago?

The cheapest round-trip flight from San Diego to Chicago recently found on Google Flights was with Frontier from $142. The cheapest one-way flight was with Frontier from $65.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from San Diego to Chicago is $165, flying from Jan 10 to Jan 17.
The cheapest United flight from San Diego to Chicago is $153, flying from Feb 14 to Feb 20.
The cheapest American flight from San Diego to Chicago is $155, flying from Feb 7 to Feb 14.
The cheapest Alaska flight from San Diego to Chicago is $155, flying from Feb 7 to Feb 14.
The cheapest Delta flight from San Diego to Chicago is $237, flying from Jan 8 to Jan 14.
The cheapest Frontier flight from San Diego to Chicago is $130, flying from Jan 24 to Feb 2.

What are the cheapest flights from San Diego to Chicago?

The cheapest round-trip flight from San Diego to Chicago starts at $142 from Sat, Feb 14 to Fri, Feb 20. The cheapest one-way flight starts at $65 and departs on Thu, Jan 15.

How long does it take to fly from San Diego to Chicago?

3 hr 50 min is the shortest flight time from San Diego to Chicago.

When should you fly to Chicago, United States?

Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.

How do I find cheap dates to fly from San Diego to Chicago?

It's easy to use Google Flights to find the cheapest days to fly from San Diego to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What is the best airline to fly from San Diego to Chicago?

What counts as the best airline for your flights from San Diego to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from San Diego to Chicago.

In terms of nonstop flights, United is the most popular. United offers 34 nonstop flights and 415 connecting flights per week. United flies from San Diego International Airport (SAN) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 21 nonstop flights and 2,587 connecting flights per week. Southwest flies from San Diego International Airport (SAN) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from San Diego to Chicago are:

American offers 21 nonstop flights and 305 connecting flights per week. American flies from San Diego International Airport (SAN) to Chicago O'Hare International Airport (ORD) .
Alaska offers 21 nonstop flights and 30 connecting flights per week. Alaska flies from San Diego International Airport (SAN) to Chicago O'Hare International Airport (ORD) .
Delta offers 369 connecting flights per week. Delta flies from San Diego International Airport (SAN) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
Frontier offers 52 connecting flights per week. Frontier flies from San Diego International Airport (SAN) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

The number of connecting flights refers to distinct flights with at least one stop between San Diego and Chicago.

Which airlines provide the cheapest flights from San Diego to Chicago?

The cheapest round-trip flight from San Diego to Chicago recently found on Google Flights was with Frontier from $142. The cheapest one-way flight was with Frontier from $65.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from San Diego to Chicago is $165, flying from Jan 10 to Jan 17.
The cheapest United flight from San Diego to Chicago is $153, flying from Feb 14 to Feb 20.
The cheapest American flight from San Diego to Chicago is $155, flying from Feb 7 to Feb 14.
The cheapest Alaska flight from San Diego to Chicago is $155, flying from Feb 7 to Feb 14.
The cheapest Delta flight from San Diego to Chicago is $237, flying from Jan 8 to Jan 14.
The cheapest Frontier flight from San Diego to Chicago is $130, flying from Jan 24 to Feb 2.

Which airlines have direct flights from San Diego to Chicago?

Southwest, United, American and Alaska fly direct from San Diego to Chicago.

There are 21 Southwest direct flights from San Diego to Chicago per week. Flights are available every day.
There are 34 United direct flights from San Diego to Chicago per week. Flights are available every day.
There are 21 American direct flights from San Diego to Chicago per week. Flights are available every day.
There are 21 Alaska direct flights from San Diego to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

Which airline provides the cheapest last-minute getaway flight from San Diego to Chicago?

The cheapest last-minute deal between San Diego and Chicago at price $422 is offered by Frontier from Fri, Nov 21 to Mon, Nov 24.

Which airlines have direct flights from San Diego to Chicago?

Southwest, United, American and Alaska fly direct from San Diego to Chicago.

There are 21 Southwest direct flights from San Diego to Chicago per week. Flights are available every day.
There are 34 United direct flights from San Diego to Chicago per week. Flights are available every day.
There are 21 American direct flights from San Diego to Chicago per week. Flights are available every day.
There are 21 Alaska direct flights from San Diego to Chicago per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

When are direct flights from San Diego to Chicago available?

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

What are the cheapest direct flights from San Diego to Chicago?

The cheapest direct (nonstop) round-trip flights between San Diego and Chicago start at $153 from Sat, Feb 14 to Fri, Feb 20 with Alaska.

How can I find nonstop flights from San Diego to Chicago?

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from San Diego to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

What are the cheapest business class flights from San Diego to Chicago?

The cheapest business class round-trip flights between San Diego and Chicago start at $727 from Thu, Jan 29 to Fri, Feb 6 with Alaska.

What are the cheapest economy class flights from San Diego to Chicago?

The cheapest economy class round-trip flights between San Diego and Chicago start at $142 from Sat, Feb 14 to Fri, Feb 20.

How can I book business class trips from San Diego to Chicago?

To book business class trips from San Diego to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

Are there any last-minute deals from San Diego to Chicago next weekend?

The best last-minute getaway deal for the next weekend between San Diego and Chicago starts at $422 from Fri, Nov 21 to Mon, Nov 24 with Frontier.

Which airline provides the cheapest last-minute getaway flight from San Diego to Chicago?

The cheapest last-minute deal between San Diego and Chicago at price $422 is offered by Frontier from Fri, Nov 21 to Mon, Nov 24.

How can I find last-minute flight deals from San Diego to Chicago?

To find last-minute flight deals from San Diego to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.