$124+ Cheap flights from Chicago (CHI) to Big Sur, CA
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SFO
Mar 7 — Mar 141
1 adult, Economy
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Find cheap flights from Chicago to Big Sur with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Big Sur are usually found in July or September, booked 83 days in advance, depart on a Thursday or Friday and return on a Wednesday
Cheap flight deals from Chicago to Big Sur
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to Big SurExplore the most affordable flight options available from Chicago to Big Sur. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.
Explore the most affordable flight options available from Chicago to Big Sur. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
- SFO
1 stop17h 39m
Frontier
Wed 2/2510:58 pm
SFO
- MDW
1 stop15h 18m
Frontier
Deal found 2/1![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/85:15 pm
ORD
- SFO
2 stops16h 33m
Frontier
Sat 4/118:09 pm
SFO
- ORD
1 stop7h 30m
Frontier
Deal found 2/1![Frontier logo]()
$244
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/217:45 am
MDW
- SFO
1 stop7h 15m
Southwest
Sat 2/286:40 am
SFO
- MDW
1 stop5h 50m
Southwest
Deal found 1/31![Southwest logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:51 am
ORD
- SFO
1 stop11h 48m
Frontier
Thu 2/268:48 am
SFO
- ORD
2 stops11h 51m
Frontier
Deal found 2/1![Frontier logo]()
$245
This Super.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:22 pm
MDW
- SFO
1 stop11h 17m
Frontier
Mon 2/233:08 pm
SFO
- MDW
1 stop6h 36m
Frontier
Deal found 2/3![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/14:16 pm
ORD
- SFO
1 stop10h 12m
Frontier
Tue 3/107:32 pm
SFO
- ORD
1 stop8h 36m
Frontier
Deal found 2/2![Frontier logo]()
$246
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:05 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Wed 3/2510:55 pm
SFO
- MDW
1 stop8h 25m
Southwest
Deal found 2/1![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:50 pm
ORD
- SFO
Nonstop5h 06m
United Airlines
Fri 3/1310:45 pm
SFO
- ORD
Nonstop4h 22m
United Airlines
Deal found 2/4![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:30 am
MDW
- SFO
2 stops10h 05m
Southwest
Wed 5/205:25 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/2![Southwest logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1011:51 am
ORD
- SFO
1 stop11h 48m
Frontier
Fri 2/2010:34 pm
SFO
- ORD
1 stop10h 12m
Frontier
Deal found 2/3![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/232:19 pm
MDW
- SFO
1 stop9h 20m
Frontier
Sat 2/288:58 am
SFO
- MDW
2 stops10h 41m
Frontier
Deal found 2/2![Frontier logo]()
$249
This American Airlines deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:38 pm
ORD
- SFO
Nonstop5h 00m
American Airlines
Wed 5/2011:28 pm
SFO
- ORD
Nonstop4h 17m
American Airlines
Deal found 2/5![American Airlines logo]()
$249
Best flights from Chicago to Big SurDiscover carefully curated flight deals from Chicago to Big Sur that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 5, 2026.
Discover carefully curated flight deals from Chicago to Big Sur that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 5, 2026.
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/159:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Sun 4/1911:25 pm
SFO
- MDW
Nonstop4h 15m
Southwest
Deal found 1/31![Southwest logo]()
$250
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/41:29 pm
MDW
- SFO
1 stop7h 07m
Delta
Mon 3/99:35 pm
SFO
- MDW
1 stop10h 21m
Delta
Deal found 2/1![Delta logo]()
$252
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/239:15 pm
ORD
- SFO
Nonstop5h 01m
United Airlines
Mon 3/3011:52 pm
SFO
- ORD
Nonstop4h 28m
United Airlines
Deal found 2/1![United Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/159:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Fri 4/175:15 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 1/31![Southwest logo]()
$250
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:20 pm
MDW
- SFO
1 stop6h 27m
Delta
Sun 3/15:45 am
SFO
- MDW
1 stop9h 52m
Delta
Deal found 2/1![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
MDW
- SFO
1 stop6h 25m
Southwest
Tue 4/282:50 pm
SFO
- MDW
1 stop6h 30m
Southwest
Deal found 1/31![Southwest logo]()
$254
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:20 pm
MDW
- SFO
1 stop6h 27m
Delta
Mon 3/25:45 am
SFO
- MDW
1 stop9h 52m
Delta
Deal found 2/2![Delta logo]()
$267
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:20 pm
ORD
- SFO
Nonstop5h 04m
United Airlines
Fri 3/136:44 pm
SFO
- ORD
Nonstop4h 15m
United Airlines
Deal found 2/3![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:10 am
MDW
- SFO
1 stop7h 35m
Southwest
Sun 3/85:05 am
SFO
- MDW
Nonstop4h 00m
Southwest
Deal found 2/2![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/231:19 pm
ORD
- SFO
1 stop7h 00m
Delta
Mon 3/3010:40 pm
SFO
- ORD
1 stop8h 30m
Delta
Deal found 2/1![Delta logo]()
$267
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:25 am
ORD
- SFO
Nonstop5h 02m
United Airlines
Wed 3/41:35 pm
SFO
- ORD
Nonstop4h 20m
United Airlines
Deal found 2/2![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:10 am
MDW
- SFO
1 stop9h 35m
Southwest
Sun 3/16:05 am
SFO
- MDW
Nonstop4h 00m
Southwest
Deal found 2/3![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:10 pm
ORD
- SFO
1 stop6h 49m
Delta
Sat 4/115:40 am
SFO
- ORD
1 stop7h 38m
Delta
Deal found 2/4![Delta logo]()
$278
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:20 pm
ORD
- SFO
Nonstop5h 04m
United Airlines
Sun 3/810:45 pm
SFO
- ORD
Nonstop4h 22m
United Airlines
Deal found 2/3![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:45 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Mon 5/111:15 pm
SFO
- MDW
1 stop8h 40m
Southwest
Deal found 2/4![Southwest logo]()
$260
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:45 pm
ORD
- SFO
Nonstop4h 53m
United Airlines
Sun 4/1211:52 pm
SFO
- ORD
Nonstop4h 28m
United Airlines
Deal found 2/3![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:25 pm
MDW
- SFO
1 stop8h 25m
Southwest
Sun 3/1511:25 pm
SFO
- MDW
Nonstop4h 05m
Southwest
Deal found 2/4![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:10 pm
ORD
- SFO
1 stop6h 49m
Delta
Thu 4/166:00 am
SFO
- ORD
2 stops13h 38m
Delta
Deal found 2/3![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:25 am
ORD
- SFO
Nonstop5h 05m
United Airlines
Mon 3/211:59 pm
SFO
- ORD
Nonstop4h 20m
United Airlines
Deal found 2/2![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:50 pm
MDW
- SFO
2 stops10h 35m
Southwest
Sun 4/265:20 am
SFO
- MDW
Nonstop4h 10m
Southwest
Deal found 2/4![Southwest logo]()
$262
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:25 am
ORD
- SFO
Nonstop4h 51m
United Airlines
Sat 4/114:55 pm
SFO
- ORD
Nonstop4h 34m
United Airlines
Deal found 2/2![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/159:00 pm
MDW
- SFO
Nonstop4h 35m
Southwest
Mon 4/209:15 pm
SFO
- MDW
1 stop8h 20m
Southwest
Deal found 1/31![Southwest logo]()
$270
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/242:35 pm
ORD
- SFO
Nonstop5h 05m
United Airlines
Sun 3/86:44 pm
SFO
- ORD
Nonstop4h 15m
United Airlines
Deal found 2/2![United Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:40 am
ORD
- SFO
Nonstop4h 58m
United Airlines
Wed 4/153:00 pm
SFO
- ORD
Nonstop4h 38m
United Airlines
Deal found 2/1![United Airlines logo]()
$307
Last-minute flights from Chicago to Big SurDiscover last-minute flight deals from Chicago to Big Sur. Data last updated February 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Big Sur. Data last updated February 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1011:51 am
ORD
- SFO
1 stop11h 48m
Frontier
Fri 2/2010:34 pm
SFO
- ORD
1 stop10h 12m
Frontier
Deal found 2/3![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:51 am
ORD
- SFO
1 stop11h 48m
Frontier
Thu 2/268:48 am
SFO
- ORD
2 stops11h 51m
Frontier
Deal found 2/1![Frontier logo]()
$245
This Super.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:22 pm
MDW
- SFO
1 stop11h 17m
Frontier
Mon 2/233:08 pm
SFO
- MDW
1 stop6h 36m
Frontier
Deal found 2/3![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/232:19 pm
MDW
- SFO
1 stop9h 20m
Frontier
Sat 2/288:58 am
SFO
- MDW
2 stops10h 41m
Frontier
Deal found 2/2![Frontier logo]()
$249
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:10 am
MDW
- SFO
1 stop9h 25m
Southwest
Sat 3/145:15 am
SFO
- MDW
Nonstop3h 55m
Southwest
Deal found 2/3![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/249:05 am
ORD
- SFO
2 stops11h 15m
Frontier
Tue 2/2410:58 pm
SFO
- ORD
1 stop9h 53m
Frontier
Deal found 2/1![Frontier logo]()
$249
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:05 am
MDW
- SFO
1 stop8h 35m
Southwest
Sat 3/75:15 am
SFO
- MDW
Nonstop3h 55m
Southwest
Deal found 2/2![Southwest logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/14:16 pm
ORD
- SFO
1 stop10h 12m
Frontier
Tue 3/107:32 pm
SFO
- ORD
1 stop8h 36m
Frontier
Deal found 2/2![Frontier logo]()
$246
This United Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:50 pm
ORD
- SFO
Nonstop5h 06m
United Airlines
Fri 3/1310:45 pm
SFO
- ORD
Nonstop4h 22m
United Airlines
Deal found 2/4![United Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:05 am
MDW
- SFO
1 stop15h 09m
Frontier
Sun 3/1510:40 pm
SFO
- MDW
1 stop21h 39m
Frontier
Deal found 2/1![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/125:01 am
ORD
- SFO
1 stop16h 13m
Frontier
Sun 3/1510:40 pm
SFO
- ORD
1 stop10h 12m
Frontier
Deal found 2/2![Frontier logo]()
$244
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/129:25 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Tue 3/1711:25 pm
SFO
- MDW
Nonstop4h 05m
Southwest
Deal found 2/3![Southwest logo]()
$250
One-way flights from Chicago to Big SurSearch for one-way flight options from Chicago to Big Sur. Find affordable one-way fares based on user searches. Data last updated February 5, 2026.
Search for one-way flight options from Chicago to Big Sur. Find affordable one-way fares based on user searches. Data last updated February 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:25 pm
MDW
- SFO
2 stops24h 55m
Frontier
Deal found 2/2![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:19 pm
ORD
- SFO
1 stop25h 01m
Frontier
Deal found 2/2![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:53 pm
MDW
- SFO
2 stops38h 10m
Frontier
Deal found 2/3![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:05 am
ORD
- SFO
1 stop18h 34m
Frontier
Deal found 2/4![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:30 am
MDW
- SFO
2 stops32h 56m
Frontier
Deal found 2/5![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/178:55 pm
ORD
- SFO
2 stops26h 43m
Frontier
Deal found 2/2![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/79:16 pm
MDW
- SFO
2 stops49h 22m
Frontier
Deal found 2/4![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:17 pm
ORD
- SFO
1 stop22h 41m
Frontier
Deal found 2/4![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:25 am
MDW
- SFO
2 stops27h 38m
Frontier
Deal found 2/2![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/264:16 pm
ORD
- SFO
2 stops18h 01m
Frontier
Deal found 2/1![Frontier logo]()
$128
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/149:40 pm
MDW
- SFO
Nonstop4h 40m
Southwest
Deal found 2/3![Southwest logo]()
$129
This American Airlines deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:45 am
ORD
- SFO
Nonstop4h 55m
American Airlines
Deal found 2/5![American Airlines logo]()
$129
Find flight deals from Chicago to Big Sur
Keep the following information in mind while searching for Chicago to Big Sur flight deals. Data was last updated February 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $244 (Kiwi.com) |
One-way from | $124 (Kiwi.com) |
Popular in | December |
Cheapest in | July |
Average price | $315 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Big Sur 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, Cheapflights users made 2,558,603 searches. Data last updated February 5, 2026.
Use the filters below to find and compare flights from Chicago to Big Sur that are best for you.
Fly from
Chicago
Fly to
Big Sur
Route
Depart
Return
Price
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 4/15
9:00 pm-11:35 pm
Nonstop4h 35m
San Francisco
Sun 4/19
11:25 pm-5:40 am
Nonstop4h 15m
$250
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 4/15
9:00 pm-11:35 pm
Nonstop4h 35m
San Francisco
Fri 4/17
5:15 am-11:25 am
Nonstop4h 10m
$250
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 3/4
1:29 pm-6:36 pm
1 stop7h 07m
San Francisco
Mon 3/9
9:35 pm-9:56 am
1 stop10h 21m
$252
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 4/18
6:00 am-10:25 am
1 stop6h 25m
San Francisco
Tue 4/28
2:50 pm-11:20 pm
1 stop6h 30m
$254
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 3/4
8:10 am-1:45 pm
1 stop7h 35m
San Francisco
Sun 3/8
5:05 am-11:05 am
Nonstop4h 00m
$260
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 2/26
6:10 am-1:45 pm
1 stop9h 35m
San Francisco
Sun 3/1
6:05 am-12:05 pm
Nonstop4h 00m
$260
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 5/7
9:45 pm-12:20 am
Nonstop4h 35m
San Francisco
Mon 5/11
1:15 pm-11:55 pm
1 stop8h 40m
$260
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 3/9
6:25 pm-12:50 am
1 stop8h 25m
San Francisco
Sun 3/15
11:25 pm-5:30 am
Nonstop4h 05m
$260
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 4/22
12:50 pm-9:25 pm
2 stops10h 35m
San Francisco
Sun 4/26
5:20 am-11:30 am
Nonstop4h 10m
$262
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 2/26
7:20 pm-11:47 pm
1 stop6h 27m
San Francisco
Sun 3/1
5:45 am-5:37 pm
1 stop9h 52m
$267
Showing 1-10 of 47 results
Best time to book a flight from Chicago to Big Sur
Have a flexible travel schedule? Discover the best time to fly to Big Sur from Chicago with our price prediction graph.
MDW-SFO
ORD-SFO
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.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Big Sur
CHI-B1G
MDW-SFO
ORD-SFO
How far ahead should I book a flight from Chicago to Big Sur?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Big Sur. Price data was last updated on January 30, 2026.
Booking 83 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Big Sur. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago to Big Sur?
Currently, October is the cheapest month in which you can book a flight from Chicago to Big Sur (average of $80). Flying from Chicago to Big Sur in November is currently the most expensive (average of $207). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to B1G?
Find hourly flight availability from Chicago to Big Sur. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 5, 2026.
One of the essential ways to save on airfare from Chicago to Big Sur is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 15% on airfare.
What is the cheapest day to fly from Chicago to Big Sur?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Big Sur. Price data was last updated on January 31, 2026.
Travelers seeking maximum savings on their Chicago to Big Sur flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Big Sur
Explore weekly flight availability from Chicago to Big Sur. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 5, 2026.
The most flights from CHI to B1G are scheduled on a Monday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).
Reviews of airlines servicing Big Sur
Get insights into the airlines that provide service to Big Sur. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Big Sur. Reviews last updated February 5, 2026.
Read through reviews of airlines operating flights from Chicago to Big Sur, such as Alaska Airlines, Southwest, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Food
7.1
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Crew
8.5
Food
7.1
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Crew
8.5
Food
7.1
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Crew
8.5
Food
7.1
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Crew
8.5
Food
7.1
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Crew
8.5
Food
7.1
Entertainment
7.0
Boarding
8.1
Comfort
7.8
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Related info for your journey
Find useful and relevant information for your journey from Chicago to Big Sur. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Big Sur
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Complete your trip
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Chicago and Big Sur flights
Browse other Chicago and Big Sur flight options. Last updated on February 5, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on February 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 10 airlines flying from Chicago to Big Sur
Discover the top 10 airlines that operate flights from Chicago to Big Sur. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$212 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$217 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$112 | Average$374 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$128 | Average$349 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$133 | Average$201 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$138 | Average$431 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$183 | Average$304 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$187 | Average$324 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$197 | Average$456 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$461 | FlexibilityNo cancel fee | On-time69% |