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Latest Flight Deals from San Diego to Chicago

Book one-way or return flights from San Diego to Chicago from as little as NZD 59. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • SAN16:07
        6h 49m
        1 stop
        ORD00:56
        Wed, May 8|San Diego - Chicago|Frontier Airlines
        NZD 59NZD 111
        46% OFF
        46% OFF
        NZD 111NZD 59
      • SAN19:09
        27h 43m
        1 stop
        ORD00:52
        Tue, May 7|San Diego - Chicago|Frontier Airlines
        NZD 66NZD 111
        41% OFF
        41% OFF
        NZD 111NZD 66
      • SAN08:14
        13h 36m
        1 stop
        ORD23:50
        Wed, Jun 5|San Diego - Chicago|Spirit Airlines
        NZD 68NZD 111
        38% OFF
        38% OFF
        NZD 111NZD 68
      • SAN08:41
        12h 48m
        1 stop
        ORD23:29
        Wed, May 8|San Diego - Chicago|Spirit Airlines
        NZD 69
        NZD 69
      • SAN12:15
        10h 17m
        1 stop
        ORD00:32
        Sat, May 11|San Diego - Chicago|Spirit Airlines
        NZD 69
        NZD 69
      • SAN08:41
        12h 48m
        1 stop
        ORD23:29
        Wed, May 15|San Diego - Chicago|Spirit Airlines
        NZD 70
        NZD 70
      • SAN09:33
        13h 23m
        1 stop
        ORD00:56
        Sat, May 11|San Diego - Chicago|Frontier Airlines
        NZD 72
        NZD 72
      • SAN20:21
        6h 39m
        1 stop
        ORD05:00
        Sat, May 18|San Diego - Chicago|Frontier Airlines
        NZD 73
        NZD 73
      • SAN08:41
        12h 48m
        1 stop
        ORD23:29
        Tue, May 14|San Diego - Chicago|Spirit Airlines
        NZD 74
        NZD 74
      • SAN16:07
        6h 49m
        1 stop
        ORD00:56
        Wed, May 15|San Diego - Chicago|Frontier Airlines
        NZD 74
        NZD 74
      • SAN13:00
        3h 5m
        Direct
        CHI14:00
        Sun, May 5|San Diego - Chicago|Frontier Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from San Diego to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from San Diego to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from San Diego to Chicago

View airlines operating flights from San Diego to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines
From NZD 59
Alaska Airlines
From NZD 148
Spirit Airlines
From NZD 150
Southwest Airlines
From NZD 165
United Airlines
From NZD 200
Sun Country Airlines
From NZD 250
American Airlines
From NZD 516
Delta Air Lines
From NZD 545
Jetblue Airways
From NZD 743
ANA airlines

Find more flights and airlines

Alternative Routes from San Diego to Chicago

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from San Diego to Chicago.

  • Cheapest
    Frontier Airlines
    SAN
    16:07
    6h 49m
    1 transfer
    ORD
    00:56
    San Diego International Airport - O'Hare International Airport
    Wed, May 8Frontier Airlines
    NZD 59
  • Frontier Airlines
    SAN
    19:09
    12h 13m
    1 transfer
    MDW
    09:22
    San Diego International Airport - Midway International Airport
    Tue, May 7Frontier Airlines
    NZD 72
  • Frontier Airlines
    SAN
    08:44
    10h 24m
    1 transfer
    RFD
    21:08
    San Diego International Airport - Chicago Rockford International Airport
    Thu, May 9Frontier Airlines
    NZD 277
  • Frontier Airlines
    SAN
    08:44
    10h 24m
    1 transfer
    RFD
    21:08
    San Diego International Airport - Chicago Rockford International Airport
    Thu, May 9Frontier Airlines
    NZD 277
    Find More Flights

How do I find the cheapest flights?

  • When are flight tickets from San Diego (SAN) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from San Diego to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from San Diego (SAN) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around NZD 473.

  • How long does it take to fly from San Diego (SAN) to Chicago (CHI) and what is the distance?

    It takes around 4 hours 18 minutes to fly from San Diego (SAN) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from San Diego (SAN) to Chicago (CHI)?

    Airlines with flights from San Diego (SAN) to Chicago (CHI): United Airlines, Emirates, Qatar Airways, Southwest Airlines, Aer Lingus and American Airlines.

How to find a cheap flight from San Diego to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from San Diego to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com
Flight Information from San Diego to Chicago

Cheapest nonstop flight price

NZD 59

Cheapest round-trip ticket price

NZD 264

Off-season for travel

April

Peak season for travel

October

Flight distance

2,786.63km

Average flight time

4 hours 18 minutes

Popular airline

American Airlines

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