Lowest Prices
Uncover the best deals on San Diego to Chicago flights by comparing fares from hundreds of airlines and agencies.
Good to Know: Cheapest and Fastest SAN - MDW Flights
Useful information for finding best airline tickets from San Diego International to Chicago Midway International on your next trip.
Cheapest Round Trip Flight
$294
Southwest Airlines
• nonstop
• 5h 50m
Feb 05 – Feb 08
The cheapest round trip flight from San Diego to Chicago (SAN-MDW-SAN) is currently $294
Cheapest One way Flight
$89
Southwest Airlines
• 1 stop
• 16h 40m
Sep 18
The cheapest one way flight from San Diego to Chicago (SAN-MDW) is currently $89
Cheapest Direct Flight
$294
Southwest Airlines
• nonstop
• 5h 50m
Feb 05
The cheapest nonstop flight from San Diego to Chicago (SAN-MDW) is currently $294
Fastest Flight
5h 50m
The fastest nonstop flight from San Diego to Chicago (SAN-MDW) takes 5h 50m
Top Airlines Flying from San Diego to Chicago
Latest Flight Deals from San Diego (SAN) to Chicago (MDW)
Compare and book low fare round-trip air tickets from San Diego to Chicago. Ideal for travelers with confirmed return itineraries.
Feb 05 - Feb 08, Economy
San Diego → Chicago
5h 50m
10:40 PM - 4:30 AM • nonstop
San Diego → Chicago
7h 10m
8:35 PM - 11:05 PM • nonstop
Southwest Airlines
Feb 05 - Feb 08, Economy
San Diego → Chicago
10h 30m
3:10 PM - 11:40 PM • 1 stop
San Diego → Chicago
7h 10m
8:35 PM - 11:05 PM • nonstop
Southwest Airlines
Feb 05 - Feb 08, Economy
San Diego → Chicago
10h 5m
8:45 AM - 4:50 PM • 1 stop
San Diego → Chicago
7h 10m
6:55 AM - 9:25 AM • nonstop
Southwest Airlines
Feb 05 - Feb 08, Economy
San Diego → Chicago
8h 50m
3:35 PM - 11:05 PM • 1 stop
San Diego → Chicago
7h 10m
8:35 PM - 11:05 PM • nonstop
Southwest Airlines
Feb 05 - Feb 08, Economy
San Diego → Chicago
10h
1:00 PM - 9:00 PM • 1 stop
San Diego → Chicago
7h 10m
8:35 PM - 11:05 PM • nonstop
Southwest Airlines
Explore competitive one-way airfare options for SAN - MDW flights. Best suited for flexible or open-ended travel plans.
Flying to Chicago soon? We've surfaced some of the most affordable last-minute flights from San Diego to Chicago, ideal for urgent plans or spontaneous trips.
Looking for the fastest way to Chicago? These direct flight options from SAN to MDW offer both convenience and value—no layovers, just straight to your destination.
Feb 05 - Feb 08, Economy
San Diego → Chicago
5h 50m
10:40 PM - 4:30 AM • nonstop
San Diego → Chicago
7h 10m
8:35 PM - 11:05 PM • nonstop
Southwest Airlines
FAQs on San Diego to Chicago Flights
What are the airports in San Diego?
SAN
What’s the most popular airline flying from SAN to MDW?
The most popular airline flying from San Diego to Chicago are
Can I fly from SAN to MDW non-stop?
Yes, you can fly SAN to MDW non-stop on
Which airlines fly nonstop between San Diego and Chicago?
The non-stop flights between San Diego and Chicago are .
What’s the earliest departure time from SAN to MDW Airport?
The earliest flight leaves SAN at 6:15 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my San Diego to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from SAN to MDW?
Read the fare rules of the San Diego to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from San Diego and Chicago?
operate flights between San Diego and Chicago
How long does a flight from San Diego to Chicago take?
It takes approximately 4 hour to fly non-stop from SAN to MDW, which is 1728.01 miles by air.
Which airlines provide the cheapest flights from San Diego (SAN) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from SAN were found on WN : USD 89
Do I need a passport to fly between SAN and MDW?
No
What’s the latest departure time from SAN to MDW ?
The last flight leaves SAN at 10:40 pm
Hotels in Chicago (MDW)
5 hotels near Chicago Midway International — compare rates from top booking sites.
4-star hotel
Doubletree By Hilton Hotel Chicago Alsip
📍 5000 West 127th Street, Alsip, Illinois 60803
Compare booking sites
Search Deals →
4-star hotel
Hyatt Regency McCormick Place
📍 2233 S Martin Luther King Dr, Chicago, Illinois 60616
Compare booking sites
Search Deals →
4-star hotel
MileNorth Hotel
📍 166 E Superior Street, Chicago, Illinois 60611
Compare booking sites
Search Deals →
4-star hotel
Sheraton Grand Chicago
📍 301 E North Water St, Chicago, Illinois 60611
Compare booking sites
Search Deals →
4-star hotel
The Westin Michigan Avenue Chicago
📍 909 North Michigan Ave, Chicago, Illinois 60611
Compare booking sites
Search Deals →
Hotel Deals in Chicago (IL)
Red Roof Inn
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
6.7/10
★★☆☆☆
Hotel
132.0 rooms
✓ Free WiFi
📍 22 West Algonquin Road, Chicago (IL)
Experience an abundance of unparalleled facilities and features at Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts. Maintain seamless communication using the complimentary Wi-Fi at hotel.For visit…
Check-in 03:00 PM · Check-out 12:00 PM
$71/night
View Deal
Choice Hotels
Radisson Hotel Schaumburg
6.9/10
★★★☆☆
Hotel
127.0 rooms
✓ Free WiFi
✓ Breakfast
📍 1550 N. Roselle Rd, Chicago (IL), Illinois
Radisson Hotel Schaumburg provides flawless service and all the necessary facilities for visitors. Stay connected with your associates, as complimentary Wi-Fi is available during your entire visit. W…
Check-in 03:00 PM · Check-out 11:00 AM
$89/night
View Deal
Wyndham Hotels & Resorts
Baymont by Wyndham Glenview
8.1/10
★★★☆☆
Hotel
95.0 rooms
✓ Free WiFi
✓ Breakfast
📍 1625 Milwaukee Ave, Chicago (IL), Illinois
At Baymont by Wyndham Glenview, exceptional service and top-notch amenities create a memorable experience for guests.Complimentary internet access is available in the hotel to ensure you stay connect…
Check-in 03:00 PM · Check-out 11:00 AM
$97/night
View Deal
Choice Hotels
Quality Inn O'Hare Airport
7.6/10
★★★☆☆
Hotel
144.0 rooms
✓ Free WiFi
✓ Breakfast
📍 3801 North Mannheim Road, Chicago (IL), Illinois
Quality Inn O'Hare Airport provides flawless service and all the necessary facilities for visitors.Stay connected with your associates, as complimentary Wi-Fi is available during your entire visit. T…
Check-in 02:00 PM · Check-out 11:30 AM
$119/night
View Deal
Wyndham Hotels & Resorts
La Quinta by Wyndham Chicago O'Hare Airport
8.3/10
★★★☆☆
Hotel
123.0 rooms
✓ Breakfast
📍 6860 Mannheim Rd, Chicago (IL), Illinois
La Quinta by Wyndham Chicago O'Hare Airport offers top-notch services and amenities, ensuring guests experience utmost comfort.Visitors can take advantage of the accessible parking options directly a…
Check-in 03:00 PM · Check-out 11:00 AM
$127/night
View Deal
No chain
Chicago South Loop
7.7/10
★★★☆☆
Hotel
232.0 rooms
✓ Free WiFi
📍 11 W 26th Street, Chicago (IL), Illinois
Chicago South Loop offers top-notch services and amenities, ensuring guests experience utmost comfort.Maintain seamless communication using the complimentary Wi-Fi at hotel. For visitors traveling by…
Check-in 03:00 PM · Check-out 11:00 AM
$164/night
View Deal
InterContinental Hotels Group
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
8.3/10
★★★★☆
Hotel
503.0 rooms
✓ Free WiFi
✓ Breakfast
📍 5440 North River Road, Chicago (IL), Illinois
Experience an abundance of unparalleled facilities and features at Crowne Plaza Chicago O'Hare Hotel & Conference Center By IHG.Share your photos and respond to emails at your convenience, thanks to …
Check-in 03:00 PM · Check-out 12:00 PM
$198/night
View Deal
Hilton Worldwide
DoubleTree by Hilton Chicago - North Shore Conference Center
8.1/10
★★★★☆
Hotel
369.0 rooms
✓ Free WiFi
✓ Breakfast
📍 9599 Skokie Boulevard, Chicago (IL), Illinois
DoubleTree by Hilton Hotel Chicago - North Shore Conference Center provides flawless service and all the necessary facilities for visitors. Remain linked during your visit by utilizing the compliment…
Check-in 3:00 PM · Check-out 12:00 PM
$200/night
View Deal
No chain
Freehand Chicago
8.1/10
★★★★☆
Hotel
215.0 rooms
✓ Free WiFi
📍 19 East Ohio Street, Chicago (IL), Illinois
At Freehand Chicago, exceptional service and top-notch amenities create a memorable experience for guests. Complimentary internet access is available in the hotel to ensure you stay connected during …
Check-in 03:00 PM · Check-out 12:00 PM
$210/night
View Deal
Also search on:
San Diego (SAN) to Chicago (MDW): Airport Information
| Origin Airport | San Diego International , San Diego, US |
| Destination Airport | Chicago Midway International , Chicago, US |
| Distance | 1728 miles |
More Flight Options for San Diego (SAN) and Chicago (MDW)
Flights from San Diego (SAN)
to Portland (PDX)
Flights from San Diego (SAN)
to San Jose (SJC)
Flights from San Diego (SAN)
to Philadelphia (PHL)
Flights from San Diego (SAN)
to Las Vegas (LAS)
Flights from San Diego (SAN)
to Sacramento (SMF)
Flights from San Diego (SAN)
to Memphis (MEM)
Flights from San Diego (SAN)
to Nashville (BNA)
Flights from San Diego (SAN)
to Los Angeles (LAX)
Flights from San Diego (SAN)
to San Antonio (SAT)
Flights from San Diego (SAN)
to Seattle (SEA)
Flights from San Diego (SAN)
to Phoenix (PHX)
Flights from San Diego (SAN)
to Vancouver (YVR)
Flights from San Diego (SAN)
to Dallas (DFW)
Flights from San Diego (SAN)
to San José del Cabo (SJD)
Flights from San Diego (SAN)
to San José del Cabo (SJD)
Flights from San Diego (SAN)
to Boston (BOS)
Flights from San Diego (SAN)
to New Orleans (MSY)
Flights from San Diego (SAN)
to Kahului (OGG)
Flights from San Diego (SAN)
to Atlanta (ATL)
Flights from San Diego (SAN)
to Montréal (YUL)
Flights from Portland (PDX)
to Chicago (ORD)
Flights from Newark (EWR)
to Chicago (ORD)
Flights from Newark (EWR)
to Chicago (ORD)
Flights from Phoenix (PHX)
to Chicago (ORD)
Flights from Atlanta (ATL)
to Chicago (ORD)
Flights from Minneapolis (MSP)
to Chicago (MDW)
Flights from Minneapolis (MSP)
to Chicago (MDW)
Flights from Los Angeles (LAX)
to Chicago (ORD)
Flights from Dallas (DFW)
to Chicago (ORD)
Flights from Dallas (DFW)
to Chicago (ORD)
Flights from Fort Lauderdale (FLL)
to Chicago (MDW)
Flights from Boston (BOS)
to Chicago (ORD)
Flights from Minneapolis (MSP)
to Chicago (ORD)
Flights from Minneapolis (MSP)
to Chicago (ORD)
Flights from Dallas (DAL)
to Chicago (MDW)
Flights from Orlando (MCO)
to Chicago (MDW)
Flights from Greensboro (GSO)
to Chicago (ORD)
Flights from Norfolk (ORF)
to Chicago (MDW)
Flights from Orlando (MCO)
to Chicago (ORD)
Flights from Houston (IAH)
to Chicago (ORD)
Cheap flights to North America (NA)
Cheap flights to United States (US)
Cheap flights to Illinois (US-IL)
Cheap flights to California (US-CA)
Cheap flights from North America (NA)
Cheap flights from United States (US)
Cheap flights from California (US-CA)
Cheap flights from Illinois (US-IL)
Flights to Chicago (MDW)
Flights to Chicago (ORD)
Flights to San Diego (SAN)
Flights from Chicago (MDW)
Flights from Chicago (MDW)
to San Diego (SAN)
Flights from Chicago (ORD)
Flights from Chicago (ORD)
to San Diego (SAN)
Flights from San Diego (SAN)
Why Fareleaders for SAN to MDW Plane Tickets
New Deals Everyday
Get the best prices on SAN to MDW flights—we update our fares daily so you never miss a saving.
No Service Fees
Compare hundreds of San Diego to Chicago flights and secure the best deals—we never add any service fees.