$678 Cheap Flights from San Luis Obispo (SBP) to Chicago (MDW)

View $678 flight on Mon, Jan 5, 2026Opens in a new window

Popular airlines from San Luis Obispo County Regional Airport (SBP) to Chicago Midway Airport (MDW)

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Cheap Flights from San Luis Obispo to Chicago (SBP-MDW)

Prices were available within the past 7 days and start at $678 for one-way flights and $1,356 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sun, Nov 23 - Wed, Nov 26
SBP
San Luis Obispo
MDW
Chicago
$1,356 Roundtrip, found 13 hours ago
$1,356
Roundtrip
found 13 hours ago
Select United flight, departing Sun, Nov 23 from San Luis Obispo to Chicago, returning Wed, Nov 26, priced at $1,356 found 13 hours ago
United
Mon, Nov 17 - Sat, Nov 22
SBP
San Luis Obispo
MDW
Chicago
$1,362 Roundtrip, found 5 days ago
$1,362
Roundtrip
found 5 days ago
Select United flight, departing Mon, Nov 17 from San Luis Obispo to Chicago, returning Sat, Nov 22, priced at $1,362 found 5 days ago
United
Mon, Dec 22 - Mon, Dec 29
SBP
San Luis Obispo
MDW
Chicago
$1,396 Roundtrip, found 3 days ago
$1,396
Roundtrip
found 3 days ago
Select United flight, departing Mon, Dec 22 from San Luis Obispo to Chicago, returning Mon, Dec 29, priced at $1,396 found 3 days ago
United
Sun, Nov 23 - Tue, Nov 25
SBP
San Luis Obispo
MDW
Chicago
$1,415 Roundtrip, found 13 hours ago
$1,415
Roundtrip
found 13 hours ago
Select United flight, departing Sun, Nov 23 from San Luis Obispo to Chicago, returning Tue, Nov 25, priced at $1,415 found 13 hours ago
United
Thu, Nov 20 - Mon, Nov 24
SBP
San Luis Obispo
MDW
Chicago
$1,416 Roundtrip, found 5 days ago
$1,416
Roundtrip
found 5 days ago
Select United flight, departing Thu, Nov 20 from San Luis Obispo to Chicago, returning Mon, Nov 24, priced at $1,416 found 5 days ago
United
Thu, Nov 20 - Mon, Nov 24
SBP
San Luis Obispo
MDW
Chicago
$1,430 Roundtrip, found 5 days ago
$1,430
Roundtrip
found 5 days ago
Select United flight, departing Thu, Nov 20 from San Luis Obispo to Chicago, returning Mon, Nov 24, priced at $1,430 found 5 days ago
United
Mon, Nov 17 - Sun, Nov 23
SBP
San Luis Obispo
MDW
Chicago
$1,435 Roundtrip, found 5 days ago
$1,435
Roundtrip
found 5 days ago
Select United flight, departing Mon, Nov 17 from San Luis Obispo to Chicago, returning Sun, Nov 23, priced at $1,435 found 5 days ago
United
Wed, Nov 19 - Wed, Nov 26
SBP
San Luis Obispo
MDW
Chicago
$1,436 Roundtrip, found 13 hours ago
$1,436
Roundtrip
found 13 hours ago
Select United flight, departing Wed, Nov 19 from San Luis Obispo to Chicago, returning Wed, Nov 26, priced at $1,436 found 13 hours ago
United
Sat, Nov 22 - Sun, Nov 23
SBP
San Luis Obispo
MDW
Chicago
$1,439 Roundtrip, found 16 hours ago
$1,439
Roundtrip
found 16 hours ago
Select United flight, departing Sat, Nov 22 from San Luis Obispo to Chicago, returning Sun, Nov 23, priced at $1,439 found 16 hours ago
United
Thu, Nov 20 - Wed, Nov 26
SBP
San Luis Obispo
MDW
Chicago
$1,445 Roundtrip, found 13 hours ago
$1,445
Roundtrip
found 13 hours ago
Select United flight, departing Thu, Nov 20 from San Luis Obispo to Chicago, returning Wed, Nov 26, priced at $1,445 found 13 hours ago

Frequently asked questions

How much does a flight from San Luis Obispo County Regional Airport (SBP) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $678 or cheap return flight from $1,356 from San Luis Obispo County Regional Airport (SBP) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from San Luis Obispo County Regional Airport (SBP) to Midway Intl. Airport (MDW)?
November is the most affordable month to fly from SBP to MDW. Traveling during an off-peak travel window is often the key to finding better fares.
What is the cheapest airline that flies from San Luis Obispo County Regional Airport (SBP) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll fly you from SBP to MDW. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
How many flights per day from San Luis Obispo County Regional Airport (SBP) to Midway Intl. Airport (MDW)?
There aren't any daily direct flights available from San Luis Obispo County Regional Airport (SBP) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be on your way before you know it.
What day of the week has the most flights from SBP to MDW?
Typically you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* However, this can vary based on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from San Luis Obispo County Regional Airport (SBP) to Midway Intl. Airport (MDW)?
Select a flight from San Luis Obispo County Regional Airport (SBP) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of cancellations. Departures after this hour have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from San Luis Obispo County Regional Airport (SBP) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from SBP to MDW are generally more expensive. For the best prices, start looking for flights early. That being said, if your travel plans are flexible, you may land a cheap ticket right before your journey.
Is it cheaper to book a SBP to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a SBP to MDW flight and hotel package with Expedia could result in significant savings. Better still, having everything in one convenient place will take the stress out of planning your trip. Simply pick your flights and choose from our wide range of stays, then customize your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from San Luis Obispo County Regional Airport (SBP) to Midway Intl. Airport (MDW)?
If you reserved your SBP to MDW flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you'd like more information.

Travel information

Origin airport
San Luis Obispo County Regional
Destination airport
Midway Intl.
Roundtrip price
$1,355
Distance
1823 mi

Book with confidence

San Luis Obispo to Chicago Flights

The cheapest times to fly from San Luis Obispo to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San Luis Obispo to Chicago are during the month of November. You can find some of the cheapest flights from San Luis Obispo to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from San Luis Obispo to Chicago

Sunday is one of the best days to book for cheap flights from San Luis Obispo to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from San Luis Obispo to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San Luis Obispo to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $678 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San Luis Obispo to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your San Luis Obispo to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

San Luis Obispo to Chicago Flights

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