Trip.com
>
Flights
>
Flights to United States
>
Flights to Illinois
>
Flights to Chicago
>
San Diego to Chicago flight
>
San Diego International Airport to Midway International Airport flight

Explore the cheapest one-way and round-trip flights from San Diego International Airport to Midway International Airport over the next 90 days, with one-way fares from $110 and round-trip from $204. Based on Trip.com's latest 7-day flight data.

    • SAN 10:30 PM
      9h 58m
      1 stop
      MDW 10:28 AM
      San Diego - Chicago | Tue, Dec 1 | Delta Air Lines
      ORD 7:25 AM
      18h 33m
      1 stop
      SAN 11:58 PM
      Chicago - San Diego | Sat, Dec 5 | Frontier Airlines
      $204 $533
      62% off
      62% off
      $533 $204
    • SAN 6:20 AM
      7h 56m
      1 stop
      MDW 4:16 PM
      San Diego - Chicago | Wed, Dec 2 | Delta Air Lines
      ORD 7:25 AM
      18h 33m
      1 stop
      SAN 11:58 PM
      Chicago - San Diego | Wed, Dec 9 | Frontier Airlines
      $204 $533
      62% off
      62% off
      $533 $204
    • SAN 1:19 PM
      7h 35m
      1 stop
      MDW 10:54 PM
      San Diego - Chicago | Sun, Dec 13 | Delta Air Lines
      ORD 7:25 AM
      18h 33m
      1 stop
      SAN 11:58 PM
      Chicago - San Diego | Wed, Dec 16 | Frontier Airlines
      $204 $533
      62% off
      62% off
      $533 $204
    • SAN 10:30 PM
      9h 58m
      1 stop
      MDW 10:28 AM
      San Diego - Chicago | Fri, Dec 11 | Delta Air Lines
      ORD 11:38 AM
      8h 33m
      1 stop
      SAN 6:11 PM
      Chicago - San Diego | Mon, Dec 14 | Frontier Airlines
      $207
      61% off
      $533 $207
    • SAN 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      San Diego - Chicago | Thu, Nov 5 | Normal Airline
      CHI 3:00 PM
      6h
      Nonstop
      SAN 4:00 PM
      Chicago - San Diego | Sat, Nov 7 | Normal Airline
      Find more flights
      Find more flights
    • Cheapest
      SAN 10:10 PM
      9h 27m
      1 stop
      MDW 9:37 AM
      San Diego - Chicago | Mon, Dec 14 | Delta Air Lines
      $110 $161
      32% off
      32% off
      $161 $110
    • SAN 10:10 PM
      9h 27m
      1 stop
      MDW 9:37 AM
      San Diego - Chicago | Thu, Dec 10 | Delta Air Lines
      $111 $161
      31% off
      31% off
      $161 $111
    • SAN 6:15 AM
      9h 46m
      1 stop
      MDW 6:01 PM
      San Diego - Chicago | Sun, Dec 6 | Delta Air Lines
      $111 $161
      31% off
      31% off
      $161 $111
    • SAN 10:30 PM
      9h 58m
      1 stop
      MDW 10:28 AM
      San Diego - Chicago | Tue, Dec 1 | Delta Air Lines
      $111
      31% off
      $161 $111
    • SAN 6:15 AM
      9h 46m
      1 stop
      MDW 6:01 PM
      San Diego - Chicago | Fri, Dec 4 | Delta Air Lines
      $111
      31% off
      $161 $111
    • SAN 6:15 AM
      8h 35m
      1 stop
      MDW 4:50 PM
      San Diego - Chicago | Sat, Dec 12 | Delta Air Lines
      $112
      30% off
      $161 $112
    • SAN 1:19 PM
      7h 35m
      1 stop
      MDW 10:54 PM
      San Diego - Chicago | Tue, Dec 15 | Delta Air Lines
      $113
      30% off
      $161 $113
    • SAN 1:19 PM
      7h 35m
      1 stop
      MDW 10:54 PM
      San Diego - Chicago | Thu, Dec 3 | Delta Air Lines
      $113
      30% off
      $161 $113
    • SAN 1:15 PM
      7h 7m
      1 stop
      MDW 10:22 PM
      San Diego - Chicago | Thu, Dec 24 | Delta Air Lines
      $114
      28% off
      $161 $114
    • SAN 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      San Diego - Chicago | Thu, Nov 5 | Normal Airline
      Find more flights
      Find more flights
    • SAN 10:30 PM
      8h 20m
      1 stop
      MDW 8:50 AM
      San Diego - Chicago | Wed, Dec 23 | Delta Air Lines
      $158 $253
      38% off
      38% off
      $253 $158
    • SAN 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      San Diego - Chicago | Thu, Nov 5 | Normal Airline
      Find more flights
      Find more flights
    • SAN 1:15 PM
      7h 7m
      1 stop
      MDW 10:22 PM
      San Diego - Chicago | Thu, Dec 24 | Delta Air Lines
      $114 $161
      28% off
      28% off
      $161 $114
    • SAN 1:19 PM
      7h 35m
      1 stop
      MDW 10:54 PM
      San Diego - Chicago | Tue, Dec 15 | Delta Air Lines
      $113 $161
      30% off
      30% off
      $161 $113
    • SAN 1:19 PM
      7h 35m
      1 stop
      MDW 10:54 PM
      San Diego - Chicago | Thu, Dec 3 | Delta Air Lines
      $113 $161
      30% off
      30% off
      $161 $113
    • SAN 6:15 AM
      8h 35m
      1 stop
      MDW 4:50 PM
      San Diego - Chicago | Sat, Dec 12 | Delta Air Lines
      $112
      30% off
      $161 $112
    • SAN 10:10 PM
      9h 27m
      1 stop
      MDW 9:37 AM
      San Diego - Chicago | Mon, Dec 14 | Delta Air Lines
      $110
      32% off
      $161 $110
    • SAN 10:10 PM
      9h 27m
      1 stop
      MDW 9:37 AM
      San Diego - Chicago | Thu, Dec 10 | Delta Air Lines
      $111
      31% off
      $161 $111
    • SAN 6:15 AM
      9h 46m
      1 stop
      MDW 6:01 PM
      San Diego - Chicago | Sun, Dec 6 | Delta Air Lines
      $111
      31% off
      $161 $111
    • SAN 6:15 AM
      9h 46m
      1 stop
      MDW 6:01 PM
      San Diego - Chicago | Fri, Dec 4 | Delta Air Lines
      $111
      31% off
      $161 $111
    • SAN 10:30 PM
      9h 58m
      1 stop
      MDW 10:28 AM
      San Diego - Chicago | Tue, Dec 1 | Delta Air Lines
      $111
      31% off
      $161 $111
    • SAN 1:00 PM
      17h 25m
      1 stop
      CHI 2:00 PM
      San Diego - Chicago | Thu, Nov 5 | Normal Airline
      Find more flights
      Find more flights

Displayed flight fares from San Diego to Chicago are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Which airline offers the cheapest flights from San Diego International Airport to Midway International Airport?

The cheapest airline flying from San Diego International Airport to Midway International Airport is Delta Air Lines (from $110) among 4 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Delta Air Lines
From $110
Frontier Airlines
From $172
Hahn Air
From $177
Alaska Airlines
From $332

Find more flights and airlines

What is the flight schedule from San Diego International Airport to Midway International Airport?

Check the schedule for flights from San Diego to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL729

    San Diego International Airport

    6:20 AM

    SAN

    4h 20m

    Nonstop

    1:40 PM

    ATL

    S M T W T F S
    Search

  2. DL1728

    Hartsfield–Jackson Atlanta International Airport

    3:30 PM

    ATL

    1h 55m

    Nonstop

    4:25 PM

    MDW

    S M T W T F S

  3. DL932

    San Diego International Airport

    12:50 PM

    SAN

    4h 21m

    Nonstop

    8:11 PM

    ATL

    S M - - - - -
    Search

  4. DL1076

    Hartsfield–Jackson Atlanta International Airport

    9:15 PM

    ATL

    1h 55m

    Nonstop

    10:10 PM

    MDW

    S M T W T F S

  5. DL1273

    San Diego International Airport

    6:20 AM

    SAN

    3h 50m

    Nonstop

    12:10 PM

    MSP

    S M T W T F S
    Search

  6. DL4714

    Minneapolis-Saint Paul International Airport

    3:08 PM

    MSP

    1h 39m

    Nonstop

    4:47 PM

    MDW

    S M T W T F S

  7. DL764

    San Diego International Airport

    10:30 PM

    SAN

    4h 25m

    Nonstop

    5:55 AM

    DTW

    S - - - - - S
    Search

  8. DL4684

    Detroit Metropolitan Wayne County Airport

    8:25 AM

    DTW

    1h 24m

    Nonstop

    8:49 AM

    MDW

    S M T W T F S

  9. DL754

    San Diego International Airport

    6:15 AM

    SAN

    4h 34m

    Nonstop

    1:49 PM

    DTW

    S M T W T F S
    Search

  10. DL4677

    Detroit Metropolitan Wayne County Airport

    5:40 PM

    DTW

    1h 20m

    Nonstop

    6:00 PM

    MDW

    S M T W T F S

  11. DL819

    San Diego International Airport

    10:40 PM

    SAN

    4h 13m

    Nonstop

    5:53 AM

    ATL

    S M - - - - -
    Search

  12. DL1063

    Hartsfield–Jackson Atlanta International Airport

    9:46 AM

    ATL

    1h 57m

    Nonstop

    10:43 AM

    MDW

    S M T W T F S
Find more flights and airlines

About San Diego International Airport and Midway International Airport

Learn about San Diego International Airport (SAN) and Midway International Airport (MDW) — including location, terminals, transportation, and travel tips.

Flight distance 2,780.79 km
Cheapest one-way ticket price $110
Cheapest return ticket price $204

FAQs for San Diego International Airport to Midway International Airport Flights

  • How long is the flight from San Diego International Airport to Midway International Airport?

    San Diego International Airport to Midway International Airport takes about 3 hours 49 minutes on average. Actual flight time may vary depending on route, weather and air traffic.
  • There are around 3 daily flights from San Diego International Airport (SAN) to Midway International Airport (MDW).
  • The earliest flight from San Diego International Airport to Midway International Airport departs at 06:15, and the last departs at 22:40, with about 14 flights per day. Flight times may change, so please check the latest departure and arrival times before you travel.
  • The route from San Diego International Airport (SAN) to Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around $255 in November, the most expensive month to book this route.
  • The earliest flight departs from San Diego International Airport (SAN) at 07:30 and arrives in Midway International Airport (MDW) at 15:55.
  • The latest flight departs from San Diego International Airport (SAN) at 19:30 and arrives in Midway International Airport (MDW) at 01:25.
    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
  • The closest airport to Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25 km.
  • One-way flights from San Diego International Airport to Midway International Airport currently start from $110, and round-trip fares start from $204. The current lowest fare is a Delta Air Lines flight departing on Mon, Dec 14; prices may vary depending on availability.
  • Based on Trip.com flight data for departures within the next 30 days with at most one stop, the average one-way price from San Diego International Airport to Midway International Airport is $196. Prices may vary depending on the departure date, airline, and availability.
  • Enter San Diego International Airport and Midway International Airport, select your departure date and number of passengers, then compare flights by price, flight duration, and baggage allowance. Once you've chosen a fare, review the change and refund rules, fill in passenger details, and pay to receive your booking confirmation.

Popular Destinations

Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

Book with no extra fees

Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, WLAN, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.