Cheap Flight Tickets from San Diego (SAN) to Chicago (MDW), Starting at $253

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

$253

WN Southwest Airlines • nonstop • 5h 55m

Oct 23 – Oct 26

The cheapest round trip flight from San Diego to Chicago (SAN-MDW-SAN) is currently $253

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Cheapest Direct Flight

$253

WN Southwest Airlines • nonstop • 5h 55m

Oct 23

The cheapest nonstop flight from San Diego to Chicago (SAN-MDW) is currently $253

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Fastest Flight

5h 50m

The fastest nonstop flight from San Diego to Chicago (SAN-MDW) takes 5h 50m

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.

Oct 23 - Oct 26, Economy
WN
San Diego → Chicago
5h 55m
6:15 AM - 12:10 PM • nonstop
WN
San Diego → Chicago
7h
2:55 PM - 5:15 PM • nonstop
$253
Southwest Airlines
Oct 23 - Oct 26, Economy
WN
San Diego → Chicago
5h 55m
6:45 PM - 12:40 AM • nonstop
WN
San Diego → Chicago
7h 5m
9:40 AM - 12:05 PM • nonstop
$253
Southwest Airlines
Oct 23 - Oct 26, Economy
WN
San Diego → Chicago
5h 50m
10:40 PM - 4:30 AM • nonstop
WN
San Diego → Chicago
7h
2:55 PM - 5:15 PM • nonstop
$253
Southwest Airlines
Oct 23 - Oct 26, Economy
WN
San Diego → Chicago
5h 55m
6:45 PM - 12:40 AM • nonstop
WN
San Diego → Chicago
10h 5m
5:15 AM - 9:20 AM • 1 stop
$255
Southwest Airlines
Oct 23 - Oct 26, Economy
WN
San Diego → Chicago
9h 10m
1:55 PM - 9:45 PM • 1 stop
WN
San Diego → Chicago
7h 5m
5:25 AM - 7:50 AM • nonstop
$257
Southwest Airlines
Oct 23 - Oct 26, Economy
WN
San Diego → Chicago
8h 55m
6:15 AM - 1:50 PM • 1 stop
WN
San Diego → Chicago
7h 5m
9:25 PM - 11:50 PM • nonstop
$257
Southwest Airlines

Fly from San Diego to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from San Diego to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

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 253
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.

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4.0-star hotel 4-star hotel

Doubletree By Hilton Hotel Chicago Alsip

📍 5000 West 127th Street, Alsip, Illinois 60803

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4.0-star hotel 4-star hotel

Hyatt Regency McCormick Place

📍 2233 S Martin Luther King Dr, Chicago, Illinois 60616

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4.0-star hotel 4-star hotel

MileNorth Hotel

📍 166 E Superior Street, Chicago, Illinois 60611

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4.0-star hotel 4-star hotel

Sheraton Grand Chicago

📍 301 E North Water St, Chicago, Illinois 60611

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4.0-star hotel 4-star hotel

The Westin Michigan Avenue Chicago

📍 909 North Michigan Ave, Chicago, Illinois 60611

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Hotel Deals in Chicago (IL)
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
Red Roof Inn

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

6.6/10
★★☆☆☆ 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

$62/night
View Deal
Suburban Studios Arlington Heights - Elk Grove
Choice Hotels

Suburban Studios Arlington Heights - Elk Grove

7.2/10
★★☆☆☆ Hotel 125.0 rooms
✓ Free WiFi

📍 2120 South Arlington Heights R, Chicago (IL), Illinois

Experience an abundance of unparalleled facilities and features at Suburban Studios Arlington Heights - Elk Grove.Maintain seamless communication using the complimentary Wi-Fi at hotel. Effortlessly …

Check-in 03:00 PM  ·  Check-out 11:00 AM

$76/night
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Baymont by Wyndham Glenview
Wyndham Hotels & Resorts

Baymont by Wyndham Glenview

8.0/10
★★★☆☆ 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

$83/night
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Chicago South Loop
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

$95/night
View Deal
Radisson Hotel Schaumburg
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

$107/night
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Freehand Chicago
No chain

Freehand Chicago

8.0/10
★★★★☆ 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

$111/night
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Millennium Hotel Knickerbocker Chicago
Millennium & Copthorne Hotels

Millennium Hotel Knickerbocker Chicago

8.2/10
★★★★☆ Hotel 306.0 rooms
✓ Free WiFi ✓ Breakfast

📍 163 East Walton Place, Chicago (IL), Illinois

Experience an abundance of unparalleled facilities and features at Millennium Knickerbocker Chicago. Maintain seamless communication using the complimentary Wi-Fi at hotel.Discovering Chicago (IL) be…

Check-in 03:00 PM  ·  Check-out 12:00 PM

$113/night
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The Chicago Hotel Collection River North
No chain

The Chicago Hotel Collection River North

6.2/10
★★★☆☆ Hotel

📍 312 W Chestnut St. Chicago, IL, Chicago (IL), Illinois

Check-in 4:00 PM  ·  Check-out 11:00 AM

$129/night
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The Saint Clair Hotel - Magnificent Mile
Independent

The Saint Clair Hotel - Magnificent Mile

8.2/10
★★★★☆ Hotel 206.0 rooms
✓ Free WiFi

📍 162 East Ontario Street, Chicago (IL), Illinois

Experience an abundance of unparalleled facilities and features at The Saint Clair Hotel - Magnificent Mile. Maintain seamless communication using the complimentary Wi-Fi at hotel.Guests can avail pa…

Check-in 04:00 PM  ·  Check-out 11:00 AM

$129/night
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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)

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