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Cheap flights from San Luis Obispo to Chicago from $135

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 10/6. 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

Alaska Airlines Logo
2:19 pm - 11:59 pmSBP-ORD
7h 40m1 stop
Alaska Airlines Logo
10:00 am - 7:01 pmORD-SBP
11h 01m1 stop
$269Alaska Airlines
Find Deal
Sat, Oct 4 - Wed, Nov 12
American Airlines Logo
12:57 pm - 11:37 pmSBP-ORD
8h 40m2 stops
American Airlines Logo
5:00 am - 12:12 pmORD-SBP
9h 12m1 stop
$274American Airlines
Find Deal
Tue, Nov 18 - Sat, Nov 22
United Airlines Logo
6:22 pm - 5:13 amSBP-ORD
8h 51m1 stop
United Airlines Logo
7:18 am - 12:16 pmORD-SBP
6h 58m1 stop
$284United Airlines
Find Deal
Thu, Sep 25 - Mon, Sep 29
Alaska Airlines Logo
7:50 pm - 6:24 amSBP-ORD
8h 34m1 stop
Alaska Airlines Logo
7:59 pm - 4:06 pmORD-SBP
22h 07m2 stops
$291Alaska Airlines
Find Deal
Thu, Oct 23 - Mon, Nov 3
Alaska Airlines Logo
7:50 pm - 6:24 amSBP-ORD
8h 34m1 stop
Alaska Airlines Logo
9:20 am - 11:26 pmORD-SBP
16h 06m1 stop
$295Alaska Airlines
Find Deal
Sat, Oct 4 - Thu, Nov 13
Alaska Airlines Logo
2:03 pm - 11:59 pmSBP-ORD
7h 56m1 stop
Alaska Airlines Logo
10:00 am - 7:01 pmORD-SBP
11h 01m1 stop
$296Alaska Airlines
Find Deal
Wed, Oct 8 - Fri, Nov 14
Alaska Airlines Logo
2:45 pm - 1:54 pmSBP-ORD
21h 09m1 stop
Alaska Airlines Logo
6:00 am - 7:00 pmORD-SBP
15h 00m1 stop
$301Alaska Airlines
Find Deal
Tue, Nov 18 - Sat, Nov 22
Alaska Airlines Logo
7:50 pm - 6:24 amSBP-ORD
8h 34m1 stop
Alaska Airlines Logo
9:20 am - 11:26 pmORD-SBP
16h 06m1 stop
$308Alaska Airlines
Find Deal
Sat, Oct 4 - Tue, Nov 11
American Airlines Logo
4:36 pm - 12:30 amSBP-ORD
5h 54m1 stop
American Airlines Logo
5:00 am - 11:36 amORD-SBP
8h 36m1 stop
$314American Airlines
Find Deal
Mon, Oct 6 - Thu, Oct 9
United Airlines Logo
12:59 pm - 9:32 pmSBP-ORD
6h 33m1 stop
United Airlines Logo
7:19 am - 12:18 pmORD-SBP
6h 59m1 stop
$359United Airlines
Find Deal
Fri, Sep 5 - Tue, Sep 9

American Airlines flights from San Luis Obispo to Chicago

Our best American Airlines deals on San Luis Obispo to Chicago flight tickets
American Airlines
Nov 18
SBP12:57 pmSan Luis Obispo County
8h 40m
2 stops
ORD11:37 pmChicago O'Hare Intl
Nov 22
ORD5:00 amChicago O'Hare Intl
9h 12m
1 stop
SBP12:12 pmSan Luis Obispo County
$274
Find similar
American Airlines
Oct 6
SBP4:36 pmSan Luis Obispo County
5h 54m
1 stop
ORD12:30 amChicago O'Hare Intl
Oct 9
ORD5:00 amChicago O'Hare Intl
8h 36m
1 stop
SBP11:36 amSan Luis Obispo County
$314
Find similar
American Airlines
Sep 5
SBP6:00 amSan Luis Obispo County
9h 30m
2 stops
ORD5:30 pmChicago O'Hare Intl
Sep 9
ORD8:25 amChicago O'Hare Intl
9h 40m
2 stops
SBP4:05 pmSan Luis Obispo County
$417
Find similar

Alaska Airlines flights from San Luis Obispo to Chicago

Our best Alaska Airlines deals on San Luis Obispo to Chicago flight tickets
Alaska Airlines
Oct 4
SBP2:19 pmSan Luis Obispo County
7h 40m
1 stop
ORD11:59 pmChicago O'Hare Intl
Nov 12
ORD10:00 amChicago O'Hare Intl
11h 01m
1 stop
SBP7:01 pmSan Luis Obispo County
$269
Find similar
Alaska Airlines
Oct 23
SBP7:50 pmSan Luis Obispo County
8h 34m
1 stop
ORD6:24 amChicago O'Hare Intl
Nov 3
ORD7:59 pmChicago O'Hare Intl
22h 07m
2 stops
SBP4:06 pmSan Luis Obispo County
$291
Find similar
Alaska Airlines
Oct 4
SBP7:50 pmSan Luis Obispo County
8h 34m
1 stop
ORD6:24 amChicago O'Hare Intl
Nov 13
ORD9:20 amChicago O'Hare Intl
16h 06m
1 stop
SBP11:26 pmSan Luis Obispo County
$295
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 August 13, 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

Sat 10/4

2:19 pm-11:59 pm

1 stop7h 40m

Chicago O'Hare Intl

Wed 11/12

10:00 am-7:01 pm

1 stop11h 01m

$269

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 11/18

12:57 pm-11:37 pm

2 stops8h 40m

Chicago O'Hare Intl

Sat 11/22

5:00 am-12:12 pm

1 stop9h 12m

$274

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Thu 9/25

6:22 pm-5:13 am

1 stop8h 51m

Chicago O'Hare Intl

Mon 9/29

7:18 am-12:16 pm

1 stop6h 58m

$284

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Thu 10/23

7:50 pm-6:24 am

1 stop8h 34m

Chicago O'Hare Intl

Mon 11/3

7:59 pm-4:06 pm

2 stops22h 07m

$291

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Sat 10/4

7:50 pm-6:24 am

1 stop8h 34m

Chicago O'Hare Intl

Thu 11/13

9:20 am-11:26 pm

1 stop16h 06m

$295

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Wed 10/8

2:03 pm-11:59 pm

1 stop7h 56m

Chicago O'Hare Intl

Fri 11/14

10:00 am-7:01 pm

1 stop11h 01m

$296

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Tue 11/18

2:45 pm-1:54 pm

1 stop21h 09m

Chicago O'Hare Intl

Sat 11/22

6:00 am-7:00 pm

1 stop15h 00m

$301

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Sat 10/4

7:50 pm-6:24 am

1 stop8h 34m

Chicago O'Hare Intl

Tue 11/11

9:20 am-11:26 pm

1 stop16h 06m

$308

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Mon 10/6

4:36 pm-12:30 am

1 stop5h 54m

Chicago O'Hare Intl

Thu 10/9

5:00 am-11:36 am

1 stop8h 36m

$314

San Luis ObispoChicago

SBP - ORD

SBPORD

San Luis Obispo County

Fri 9/5

12:59 pm-9:32 pm

1 stop6h 33m

Chicago O'Hare Intl

Tue 9/9

7:19 am-12:18 pm

1 stop6h 59m

$359

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 $339. 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 $375.

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.

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

Best Price Found

$135

Fastest flight time

5h 54m

Direct flights

None

Airports in Chicago

1 airport
The best one-way flight to Chicago from San Luis Obispo in the past 72 hours is $135. The best round-trip flight deal from San Luis Obispo to Chicago found on momondo in the last 72 hours is $269.
The fastest flight from San Luis Obispo to Chicago takes 5h 54m
There are no direct flights from San Luis Obispo to Chicago. Popular non-direct route for this connection is San Luis Obispo County Airport - Chicago O'Hare Intl Airport.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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 54m, 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
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $362Free CancellationRating
7.4
8,920 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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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