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Cheap flights from San Luis Obispo to Chicago from $203

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Luis Obispo to Chicago departing on 12/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from San Luis Obispo to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
5:25 pm - 5:02 amSBP-ORD
9h 37m1 stop
Alaska Airlines Logo
9:00 am - 4:34 pmORD-SBP
9h 34m1 stop
$279Alaska Airlines
Find Deal
Tue, Jan 6 - Sat, Jan 10
Alaska Airlines Logo
5:25 pm - 5:02 amSBP-ORD
9h 37m1 stop
Alaska Airlines Logo
3:44 pm - 11:20 pmORD-SBP
9h 36m1 stop
$289Alaska Airlines
Find Deal
Tue, Jan 6 - Fri, Jan 16
Hawaiian Airlines Logo
12:19 pm - 11:59 pmSBP-ORD
9h 40m1 stop
Hawaiian Airlines Logo
3:07 pm - 11:17 pmORD-SBP
10h 10m1 stop
$290Hawaiian Airlines
Find Deal
Fri, Feb 20 - Tue, Feb 24
United Airlines Logo
5:00 am - 1:24 pmSBP-ORD
6h 24m1 stop
United Airlines Logo
6:29 pm - 11:44 pmORD-SBP
7h 15m1 stop
$294United Airlines
Find Deal
Fri, Jan 23 - Sun, Jan 25
Alaska Airlines Logo
5:25 pm - 5:02 amSBP-ORD
9h 37m1 stop
Alaska Airlines Logo
3:44 pm - 11:20 pmORD-SBP
9h 36m1 stop
$298Alaska Airlines
Find Deal
Mon, Jan 5 - Mon, Jan 12
American Airlines Logo
12:50 pm - 11:44 pmSBP-ORD
8h 54m2 stops
American Airlines Logo
1:25 pm - 6:30 pmORD-SBP
7h 05m1 stop
$304American Airlines
Find Deal
Fri, Jan 23 - Sun, Jan 25
Alaska Airlines Logo
5:14 pm - 5:10 pmSBP-ORD
21h 56m2 stops
Alaska Airlines Logo
3:44 pm - 11:20 pmORD-SBP
9h 36m1 stop
$306Alaska Airlines
Find Deal
Tue, Jan 27 - Fri, Jan 30
Alaska Airlines Logo
3:47 pm - 2:58 pmSBP-ORD
21h 11m2 stops
Alaska Airlines Logo
3:07 pm - 11:17 pmORD-SBP
10h 10m1 stop
$317Alaska Airlines
Find Deal
Mon, Feb 23 - Sat, Feb 28
Alaska Airlines Logo
5:25 pm - 5:02 amSBP-ORD
9h 37m1 stop
Alaska Airlines Logo
6:06 pm - 11:20 pmORD-SBP
31h 14m2 stops
$326Alaska Airlines
Find Deal
Mon, Jan 5 - Tue, Jan 13
American Airlines Logo
12:50 pm - 11:44 pmSBP-ORD
8h 54m2 stops
American Airlines Logo
3:23 pm - 10:16 pmORD-SBP
8h 53m2 stops
$340American Airlines
Find Deal
Fri, Jan 23 - Sun, Jan 25

Alaska Airlines flights from San Luis Obispo to Chicago

Our best Alaska Airlines deals on San Luis Obispo to Chicago flight tickets
Alaska Airlines
Jan 6
SBP5:25 pmSan Luis Obispo County
9h 37m
1 stop
ORD5:02 amChicago O'Hare Intl
Jan 14
ORD3:44 pmChicago O'Hare Intl
9h 36m
1 stop
SBP11:20 pmSan Luis Obispo County
$279
Find similar
Alaska Airlines
Jan 6
SBP5:25 pmSan Luis Obispo County
9h 37m
1 stop
ORD5:02 amChicago O'Hare Intl
Jan 12
ORD9:00 amChicago O'Hare Intl
9h 34m
1 stop
SBP4:34 pmSan Luis Obispo County
$289
Find similar
Alaska Airlines
Jan 5
SBP5:25 pmSan Luis Obispo County
9h 37m
1 stop
ORD5:02 amChicago O'Hare Intl
Jan 12
ORD3:44 pmChicago O'Hare Intl
9h 36m
1 stop
SBP11:20 pmSan Luis Obispo County
$298
Find similar

American Airlines flights from San Luis Obispo to Chicago

Our best American Airlines deals on San Luis Obispo to Chicago flight tickets
American Airlines
Feb 20
SBP7:10 pmSan Luis Obispo County
8h 06m
1 stop
ORD5:16 amChicago O'Hare Intl
Feb 24
ORD10:48 amChicago O'Hare Intl
9h 51m
2 stops
SBP6:39 pmSan Luis Obispo County
$384
Find similar
American Airlines
Feb 20
SBP12:42 pmSan Luis Obispo County
8h 55m
2 stops
ORD11:37 pmChicago O'Hare Intl
Feb 24
ORD8:25 amChicago O'Hare Intl
12h 14m
2 stops
SBP6:39 pmSan Luis Obispo County
$389
Find similar
American Airlines
Feb 20
SBP12:45 pmSan Luis Obispo County
7h 38m
1 stop
ORD10:23 pmChicago O'Hare Intl
Feb 24
ORD9:25 amChicago O'Hare Intl
11h 14m
2 stops
SBP6:39 pmSan Luis Obispo County
$394
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San Luis Obispo to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 26, 2025.
Use the filters below to find and compare flights from San Luis Obispo to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 1/6

5:25 pm-5:02 am

1 stop9h 37m

Chicago O'Hare Intl

Sat 1/10

9:00 am-4:34 pm

1 stop9h 34m

$279

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 1/6

5:25 pm-5:02 am

1 stop9h 37m

Chicago O'Hare Intl

Fri 1/16

3:44 pm-11:20 pm

1 stop9h 36m

$289

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 2/20

12:19 pm-11:59 pm

1 stop9h 40m

Chicago O'Hare Intl

Tue 2/24

3:07 pm-11:17 pm

1 stop10h 10m

$290

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 1/23

5:00 am-1:24 pm

1 stop6h 24m

Chicago O'Hare Intl

Sun 1/25

6:29 pm-11:44 pm

1 stop7h 15m

$294

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Mon 1/5

5:25 pm-5:02 am

1 stop9h 37m

Chicago O'Hare Intl

Mon 1/12

3:44 pm-11:20 pm

1 stop9h 36m

$298

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 1/23

12:50 pm-11:44 pm

2 stops8h 54m

Chicago O'Hare Intl

Sun 1/25

1:25 pm-6:30 pm

1 stop7h 05m

$304

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 1/27

5:14 pm-5:10 pm

2 stops21h 56m

Chicago O'Hare Intl

Fri 1/30

3:44 pm-11:20 pm

1 stop9h 36m

$306

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Mon 2/23

3:47 pm-2:58 pm

2 stops21h 11m

Chicago O'Hare Intl

Sat 2/28

3:07 pm-11:17 pm

1 stop10h 10m

$317

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Mon 1/5

5:25 pm-5:02 am

1 stop9h 37m

Chicago O'Hare Intl

Tue 1/13

6:06 pm-11:20 pm

2 stops31h 14m

$326

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 1/23

12:50 pm-11:44 pm

2 stops8h 54m

Chicago O'Hare Intl

Sun 1/25

3:23 pm-10:16 pm

2 stops8h 53m

$340

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from San Luis Obispo to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between San Luis Obispo and Chicago?

What is the cheapest month to fly to Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from San Luis Obispo, with most prices found around $317. If you’re not able to fly to Chicago in August, then February is your next best option. Flight prices from San Luis Obispo to Chicago during February average around $372.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $545. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from San Luis Obispo to Chicago for around $752.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from San Luis Obispo to Chicago during this time can be as low as $500. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $688.

How have San Luis Obispo to Chicago flight prices changed over time?

When to book flights from San Luis Obispo to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from San Luis Obispo to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San Luis Obispo to Chicago (SBP to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Luis Obispo to Chicago

Fastest flight time

5h 46m

Direct flights

None
The fastest flight from San Luis Obispo to Chicago takes 5h 46m
There are no direct flights from San Luis Obispo to Chicago. There are no popular flight routes from San Luis Obispo to Chicago.
Search flight deals

  • How far is San Luis Obispo County to Chicago by plane?

    Chicago is 1827.9 mi away from San Luis Obispo County. Flights usually cover this in 5h 46m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from San Luis Obispo County Airport to Chicago?

    Prices for flights from San Luis Obispo County Airport to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from San Luis Obispo County Airport to Chicago?

  • How old do you have to be to fly from San Luis Obispo County Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from San Luis Obispo County Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from San Luis Obispo to Chicago?

Best airlines flying from San Luis Obispo to Chicago

Compare and see reviews for airlines that fly from San Luis Obispo to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $274Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
United AirlinesPriceFrom $362Free CancellationRating
7.4
9,050 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
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Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from San Luis Obispo to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from San Luis Obispo to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from San Luis Obispo to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from San Luis Obispo on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from San Luis Obispo to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San Luis Obispo to Chicago.

I’m not ready to book a flight from San Luis Obispo to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from San Luis Obispo and alert you when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport