In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What is the cheapest time of day to fly from SBP to MDW?

When flying from San Luis Obispo to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Most accurate provider : When it comes to deals on San Luis Obispo-Chicago Midway Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on San Luis Obispo-Chicago Midway Airport flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from San Luis Obispo-Chicago Midway Airport flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on San Luis Obispo-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Luis Obispo-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

What airport do you fly from for flights from San Luis Obispo to Chicago Midway?

San Luis Obispo County (SBP) is the airport you will fly out of if you book a flight from San Luis Obispo to Chicago Midway. You should not have trouble finding flights to Chicago Midway from County; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the San Luis Obispo airport to Chicago Midway. It is only a 3.3 mi journey to County (SBP) from San Luis Obispo’s city center.

Can I find deals for flights from San Luis Obispo to Midway that include hotel bookings?

Yes. In addition to deals on San Luis Obispo to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from San Luis Obispo to Midway?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Luis Obispo to Midway.

Can I find deals for business class flights from San Luis Obispo to Midway?

Yes. Cheapflights offers flight deals from San Luis Obispo to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$619+ Cheap Flights from San Luis Obispo to Chicago Midway Airport

Q: E

Most trusted provider : When it comes to deals on San Luis Obispo-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Luis Obispo-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Q: What airport do you fly from for flights from San Luis Obispo to Chicago Midway?

San Luis Obispo County (SBP) is the airport you will fly out of if you book a flight from San Luis Obispo to Chicago Midway. You should not have trouble finding flights to Chicago Midway from County; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the San Luis Obispo airport to Chicago Midway. It is only a 3.3 mi journey to County (SBP) from San Luis Obispo’s city center.

Q: Can I find deals for flights from San Luis Obispo to Midway that include hotel bookings?

Yes. In addition to deals on San Luis Obispo to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

Q: How can I find direct flights from San Luis Obispo to Midway?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Luis Obispo to Midway.

Q: Can I find deals for business class flights from San Luis Obispo to Midway?

Yes. Cheapflights offers flight deals from San Luis Obispo to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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Cheap flight deals from San Luis Obispo to Midway

One-way

One-way flights from San Luis Obispo to Midway
Search for one-way flight options from San Luis Obispo to Midway. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.

Thu 10/86:30 pm -

3 stops51h 13m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/4

$619

Find flight deals from San Luis Obispo to Midway

Most accurate provider	Expedia 1 star
Most trusted provider	Expedia 3 stars
Popular in	October
Cheapest in	March
Average price	$573

Provider with most accurate pricing for San Luis Obispo County-Chicago Midway flight deals.

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Provider most trusted by Cheapflights users for San Luis Obispo County-Chicago Midway flights.

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Highest demand for flights based on searches. 18% potential increase in price ($117 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).

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Average for round-trip flights in September 2026

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San Luis ObispoChicago

SBP San Luis Obispo County - MDW Chicago Midway

SBPMDW

San Luis Obispo County

Thu 10/8

6:30 pm-11:43 pm

3 stops51h 13m

Chicago Midway

Wed 12/31

12:00 am-10:00 pm

Nonstop0h 00m

$619

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/4

Sorted by cheapest first

Most accurate provider: When it comes to deals on San Luis Obispo-Chicago Midway Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on San Luis Obispo-Chicago Midway Airport flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from San Luis Obispo-Chicago Midway Airport flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on San Luis Obispo-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Luis Obispo-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from San Luis Obispo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San Luis Obispo with our price prediction graph.

SBP-MDW

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

What airport do you fly from for flights from San Luis Obispo to Chicago Midway?
San Luis Obispo County (SBP) is the airport you will fly out of if you book a flight from San Luis Obispo to Chicago Midway. You should not have trouble finding flights to Chicago Midway from County; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the San Luis Obispo airport to Chicago Midway. It is only a 3.3 mi journey to County (SBP) from San Luis Obispo’s city center.
Can I find deals for flights from San Luis Obispo to Midway that include hotel bookings?
Yes. In addition to deals on San Luis Obispo to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from San Luis Obispo to Midway?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Luis Obispo to Midway.
Can I find deals for business class flights from San Luis Obispo to Midway?
Yes. Cheapflights offers flight deals from San Luis Obispo to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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$619+ Cheap flights from San Luis Obispo (SBP) to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/8. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from San Luis Obispo to Midway with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from San Luis Obispo to Midway

One-way flights from San Luis Obispo to MidwaySearch for one-way flight options from San Luis Obispo to Midway. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.

Search for one-way flight options from San Luis Obispo to Midway. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.

Find flight deals from San Luis Obispo to Midway

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Use the filters below to find and compare flights from San Luis Obispo to Chicago Midway Airport that are best for you.

Best time to book a flight from San Luis Obispo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San Luis Obispo with our price prediction graph.

Related info for your journey

What airport do you fly from for flights from San Luis Obispo to Chicago Midway?

Can I find deals for flights from San Luis Obispo to Midway that include hotel bookings?

How can I find direct flights from San Luis Obispo to Midway?

Can I find deals for business class flights from San Luis Obispo to Midway?

Traveling to a place near Chicago Midway Airport?

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Complete your trip

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Other flights to Midway

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One-way flights from San Luis Obispo to Midway
Search for one-way flight options from San Luis Obispo to Midway. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.