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Cheap Flights from San Diego to Chicago Midway

Compare San Diego to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from San Diego to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from San Diego to Chicago Midway Airport? If you want to travel next month, return fares start from R 3,328. Find the lowest prices on one-way and return tickets right here.
Chicago.R 1,217 per passenger.Departing Thu, 23 Apr.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Thu, 23 Apr, arriving in Chicago Midway.Price includes taxes and charges.From R 1,217, select.
Chicago.R 1,367 per passenger.Departing Tue, 5 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Tue, 5 May, arriving in Chicago Midway.Price includes taxes and charges.From R 1,367, select.
Chicago.R 1,649 per passenger.Departing Tue, 19 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Tue, 19 May, arriving in Chicago Midway.Price includes taxes and charges.From R 1,649, select.
Chicago.R 1,659 per passenger.Departing Sat, 25 Apr.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Sat, 25 Apr, arriving in Chicago Midway.Price includes taxes and charges.From R 1,659, select.
Chicago.R 2,343 per passenger.Departing Tue, 23 Jun.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Tue, 23 Jun, arriving in Chicago Midway.Price includes taxes and charges.From R 2,343, select.
Chicago.R 2,356 per passenger.Departing Mon, 20 Jul.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Mon, 20 Jul, arriving in Chicago Midway.Price includes taxes and charges.From R 2,356, select.
Chicago.R 2,529 per passenger.Departing Tue, 4 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Tue, 4 Aug, arriving in Chicago Midway.Price includes taxes and charges.From R 2,529, select.
Chicago.R 2,724 per passenger.Departing Tue, 21 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Tue, 21 Jul, arriving in Chicago Midway.Price includes taxes and charges.From R 2,724, select.
Chicago.R 2,724 per passenger.Departing Sun, 7 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Sun, 7 Jun, arriving in Chicago Midway.Price includes taxes and charges.From R 2,724, select.
Chicago.R 2,739 per passenger.Departing Tue, 20 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Tue, 20 Oct, arriving in Chicago Midway.Price includes taxes and charges.From R 2,739, select.
Chicago.R 2,739 per passenger.Departing Wed, 12 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Wed, 12 Aug, arriving in Chicago Midway.Price includes taxes and charges.From R 2,739, select.
Chicago.R 2,755 per passenger.Departing Thu, 17 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Thu, 17 Sep, arriving in Chicago Midway.Price includes taxes and charges.From R 2,755, select.
Chicago.R 3,071 per passenger.Departing Sat, 26 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from San Diego International on Sat, 26 Dec, arriving in Chicago Midway.Price includes taxes and charges.From R 3,071, select.
Chicago.R 3,467 per passenger.Departing Mon, 30 Mar.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Mon, 30 Mar, arriving in Chicago Midway.Price includes taxes and charges.From R 3,467, select.
Chicago.R 4,454 per passenger.Departing Mon, 30 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Mon, 30 Mar, arriving in Chicago Midway.Price includes taxes and charges.From R 4,454, select.

Find the cheapest month to fly from San Diego to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Diego to Chicago Midway flights are currently cheapest in April.
Mar
from R 3,467
Apr
from R 1,217
May
from R 1,367
Jun
from R 2,343
Jul
from R 2,356
Aug
from R 2,529
Sep
from R 2,755
Oct
from R 2,739
Nov
Find prices
Dec
from R 3,071
Jan
Find prices
Feb
Find prices

Direct flights from San Diego to Chicago Midway

San Diego to Chicago Midway: Alternative routes

Compare routes from San Diego to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

14km from central Chicago
Closest
from R 1,217
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from R 1,212
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from R 2,025
Search flights

San Diego to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 1,217
Cheapest month to flyApril
Average flight time3 hrs, 58 mins
Most popular airlineSouthwest Airlines
Average flights per week26

Finding cheap flights from San Diego to Chicago Midway: Frequently asked questions

The best price we found for a return flight from San Diego to Chicago Midway is R 2,804. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
3 hours and 58 minutes is the average flight time from San Diego to Chicago Midway.
Southwest Airlines flies direct from San Diego to Chicago Midway.
As of March 2026, there are 26 flights per week flying from San Diego to Chicago Midway.
The cheapest month to fly from San Diego to Chicago Midway is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from San Diego to Chicago Midway Airport on Tuesday, 12 May 2026.
Yes – the average flight time is 3 hours and 58 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Travelling from San Diego to Chicago Midway International Airport (MDW): What you need to know

  • Start planning your trip by checking out where you'll catch your flight from San Diego to Chicago Midway International Airport (MDW). Explore the options for leaving from San Diego International Airport (SAN) or McClellan-Palomar Airport (CLD), the city's main airports.

  • Jump on a direct San Diego to Chicago Midway International Airport flight and you'll be in the air for around 4 hours.

  • Chicago is two hours ahead of San Diego. Chicago Midway International Airport is located in Chicago, which follows the UTC-5 timezone.

  • San Diego International Airport (SAN) to Chicago Midway International Airport (MDW) is the most popular route. There are 12 direct flights a week to pick from. If you have plans before you fly, hop on the last flight with Southwest Airlines at 7:55pm. Opt for the first SAN to MDW departure with Southwest Airlines at 6:30am if getting there sooner works for you.

  • To ensure you get on your flight from San Diego to MDW, leave enough time for things like baggage drop and finding your gate. Arriving two hours ahead of international departures and one hour before domestic flights is the general rule.

  • Planning to travel during a peak period like public or school holidays? Expect longer queues at check-in and security. Give yourself extra leeway and arrive up to four hours before international flights and two hours ahead of domestic departures.

Airports in San Diego

San Diego International Airport (SAN)

  • Get there in one go from San Diego International Airport (SAN). Direct flights from San Diego to Chicago Midway International Airport (MDW) can be booked from here.

  • When taking off from SAN, you can take a direct flight from San Diego to Chicago Midway International Airport with Southwest Airlines.

  • Most passengers choose to fly with Southwest Airlines between SAN and MDW.

  • The carrier with the best punctuality score on this route is Southwest Airlines. Its services land as planned 71.53% of the time.

  • SAN is around 5 kilometres from central San Diego. If you're catching a cab, ride-sharing or driving from the centre, it'll take you 10 minutes or so to get there, depending on the traffic. If you're planning to take public transport, expect the trip time to be around 20 minutes.

  • Have an early flight from San Diego to Chicago Midway International Airport? Avoid rushing to the terminal (and get some extra shut-eye) by picking one of these hotels close to San Diego International Airport:

  • When it comes to San Diego International Airport's on-time performance, 71.38% of flights complete their journey on time.

  • SAN's address is N Harbour Dr.

McClellan-Palomar Airport (CLD)

  • On public transport, you can travel from central San Diego to CLD in about 2 hours 15 minutes. The airport is roughly 56 kilometres away, and making the journey by car takes approximately 40 minutes.

  • Start your holiday sooner with an additional night away from home. Before your San Diego to MDW flight, kick back in one of these hotels close to McClellan-Palomar Airport:

About Chicago Midway International Airport (MDW)

  • The last thing you need is a lengthy journey to your hotel if you're getting in late on a flight from San Diego to Chicago Midway International Airport. Make yourself comfy at one of these accommodation options near MDW instead:

  • Get your adventure underway by picking up a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget to explore Chicago and beyond.

  • Booking your vehicle around four weeks ahead of your San Diego to Chicago Midway International Airport flight can help you lock in a great deal.

  • You'll find MDW at 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • Chicago Midway International Airport is around 14 kilometres from central Chicago. How long it takes to get to the centre in a cab or car hire depends on the time of day. Do a little research before your trip.

  • It typically takes 45 minutes if you're travelling by public transport.

How to find the cheapest flights from San Diego to Chicago Midway International Airport (MDW)

  • R 1,217 is the best price for a one-way ticket from San Diego to Chicago Midway International Airport. Return flights start from R 2,804. These prices can change based on demand and availability.

  • To snag cheap flights from San Diego to MDW, book your ticket one month ahead of your planned departure.

  • June is when you're most likely to find a good deal on a San Diego to Chicago Midway International Airport ticket. If you want to travel during a different time of year, the 'Whole month' tool will show you the lowest prices across every month.

  • Save time looking for cheap plane tickets from San Diego to MDW by creating a Price Alert. We'll send you an email or push notification on the app when prices go down.

  • Tailor your travel plans using filters. Select your departure and arrival times, total journey duration and airlines. You can also sort your results by 'Best,' 'Cheapest' or 'Fastest' flights from San Diego to Chicago Midway International Airport.

The best time to fly from San Diego to Chicago Midway International Airport (MDW)

  • May is the quietest month for flights from San Diego to Chicago Midway International Airport (MDW), while July is the most popular. Pick the ideal time to visit Chicago based on whether you prefer a laid-back vibe or a more bustling atmosphere.

  • Before locking in your San Diego to MDW plane ticket, consider what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • January sees temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from San Diego to Chicago Midway International Airport around that time if you want to travel when it's cooler.

More about Chicago

Explore more of the United States

  • You've seen Chicago, now it's time to explore other corners of the United States. Journey around 257 kilometres south-east to Indianapolis to check off its top sights. From 9-11 Memorial to Lucas Oil Stadium and Eiteljorg Museum, you'll have a packed itinerary ahead.

  • Milwaukee is another standout destination in the United States and is around 137 kilometres north of Chicago. No journey is complete without experiencing Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

Plan the rest of your trip from San Diego to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.