Cheap flights from San Diego to Chicago Midway from $194

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Cheap San Diego - Chicago Midway flight offers

Find cheap flight tickets and last-minute flight deals from San Diego to Chicago Midway

Southwest Airlines
Thu, 07/02 (SAN) San Diego -> (MDW) Chicago
Direct
Southwest Airlines
Tue, 07/07 (MDW) Chicago -> (SAN) San Diego
Direct

Price found 10 days ago
from $194
Southwest Airlines
Thu, 07/02 (SAN) San Diego -> (MDW) Chicago
Direct
Southwest Airlines
Tue, 07/07 (MDW) Chicago -> (SAN) San Diego
Direct

Price found 10 days ago
from $194

Info about flights from San Diego to Chicago Midway

Some useful info about flights from San Diego to Chicago Midway to help you plan your next trip

Best price last 15 days $194
Average flight duration 3h 53m
Cheapest month March
Average number of flights per week 3
First flight time 06:15
Last flight time 22:40
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Top airlines on the route San Diego - Chicago Midway

Airlines providing flights to Chicago Midway from San Diego

How much is a ticket from San Diego to Chicago Midway?

Flight prices from San Diego to Chicago change depending on demand and time of booking.

$194 is the best price recorded in the last 15 days.

Flying at off-peak hours — such as early morning or late evening — can help you save. Also, the best deals tend to appear in the weeks leading up to departure.

Are there multiple airports in San Diego and Chicago?

If your departure or arrival city has more than one airport, it's worth comparing all of them for timing and pricing.

  • Airports in San Diego: McClellan-Palomar is an alternative to San Diego - International.
  • Airports in Chicago: 3 airports are available in Chicago - Midway, O'Hare, Rockford.

If you're traveling with a group or bulky luggage, look into parking or transport options. Alternative airports may offer faster transfers or better rates.

Flights from San Diego - International to Chicago - Midway

Refine your flight search from San Diego to Chicago Midway

With Jetcost, it’s easy to narrow down results to find flights that match your schedule and preferences. You can filter by airline, price, trip type, and more — including offers from Expedia, eDreams, and top carriers.

Other popular destinations

Also looking at United States? These cities are trending: Atlanta, Los Angeles, Miami, New York City, Orlando.

Online agencies can show different offers for the same flight — it’s worth comparing. Filters let you narrow things down further, like selecting a specific time slot to find flights that suit you best.

Frequently Asked Questions

Frequently asked questions about flights from San Diego to Chicago Midway.

How much does an airline ticket from San Diego to Chicago Midway cost?

The lowest price recorded in the last 15 days for a flight from San Diego to Chicago Midway is $194.

How far is San Diego from Chicago?

San Diego is about 1725 mi from Chicago.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the airports in San Diego?

San Diego has another airport: McClellan-Palomar.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Atlanta, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from San Diego to Chicago?

The best time to book a flight from San Diego to Chicago is 2 months in advance, while the worst time is 2 weeks in advance.

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

The cheapest month to fly from San Diego to Chicago is March.

What is the most expensive month to fly from San Diego to Chicago?

The most expensive month to fly from San Diego to Chicago is July.

What is the best day of the week to fly from San Diego to Chicago?

For flights from San Diego to Chicago Friday is on average the cheapest day to fly, while Sunday is the most expensive day to fly.