Cheap Flights from San Francisco to Chicago
Browse current best options from San Francisco. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
San Francisco
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from San Francisco to Chicago
Explore current cheapest deals departing from San Francisco to Chicago
Round trip
Sort by: Cheapest
September 15 - September 29
SFO - Chicago
$219
$214
Round trip
September 9 - September 15
SFO - Chicago
$232
$214
Round trip
September 23 - September 30
SFO - Chicago
$249
$214
Round trip
September 1 - September 15
SFO - Chicago
$200
$214
Round trip
August 12 - August 18
SFO - Chicago
$303
$215
Round trip
August 11 - August 12
SFO - Chicago
$269
$215
Round trip
September 28 - October 28
SFO - Chicago
$270
$215
Round trip
September 28 - October 21
SFO - Chicago
$271
$215
Round trip
September 29 - October 21
SFO - Chicago
$272
$215
Round trip
September 29 - October 28
SFO - Chicago
$271
$215
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from San Francisco to Chicago
How much is a round trip from San Francisco to Chicago
Regular price: $215 - $357
Prices for flights from San Francisco to Chicago are currently within the regular range.
The regular price range for flights from San Francisco to Chicago is between $215 and $357. The current lowest deal is $215 with Frontier Airlines, for travel from Sep 28-Oct 28.
now $215
Low $215
High $357
The cheapest time to fly from San Francisco to Chicago
The cheapest month to fly from San Francisco to Chicago is April, with a median price of $232. The most expensive month is November, with a median price of $904. Generally, prices are lower from January to December.
April
Flights from $232
November
Flights from $904
Direct flights from San Francisco to Chicago
United Airlines
Last-minute flights going from San Francisco to Chicago
Mon, Jul 6
SFO - Chicago
San Francisco (SFO) - Chicago (ORD)
$245
$315
One-way
Mon, Jul 6
SFO - Chicago
San Francisco (SFO) - Chicago (ORD)
$242
$315
One-way
Tue, Jul 7
SFO - Chicago
San Francisco (SFO) - Chicago (ORD)
$262
$315
One-way
Tue, Jul 7
SFO - Chicago
San Francisco (SFO) - Chicago (ORD)
$245
$315
One-way
Wed, Jul 8
SFO - Chicago
San Francisco (SFO) - Chicago (ORD)
$249
$315
One-way
Wed, Jul 8
SFO - Chicago
San Francisco (SFO) - Chicago (ORD)
$233
$315
One-way
Biggest price drops on these dates for flights from San Francisco to Chicago
Dec 16 - Dec 24
$448 → $365
19%
Dec 17 - Dec 25
$448 → $374
16%
Dec 16 - Dec 25
$444 → $374
16%
Dec 2 - Dec 5
$395 → $335
15%
Popular Airports to fly from San Francisco to Chicago
San Francisco - Chicago route insights
💸 Price insights
Recent fares are above the typical level.
Recent fares from San Francisco to Chicago are above the typical level for the last 90 days.
📅 Best time to fly
April, December, and January are historically cheapest.
Historically, the cheapest months to fly from San Francisco to Chicago are April ($232), December ($233), and January ($244).
⏱️ Flight duration
Flights typically take 12h 1m.
The median flight duration from San Francisco to Chicago is 12h 1m, covering a distance of 2979 km.
✈️ Airlines & availability
Direct flights are available.
Approximately 44.8% of recent deals for this route are for direct flights.
🏆 Airline highlight
United Airlines offers direct flights.
United Airlines is one of the airlines that offers direct flights from San Francisco to Chicago.
🎯 Booking tip
Deals are frequent for this route.
Historically, deals for flights from San Francisco to Chicago are frequent, with over 1 deal per day.
San Francisco main airports to depart from
San Francisco International (SFO)
San Francisco International is a good option for flights from San Francisco to Chicago.
📍 ~20 km from city center (reachable by car or train)
💸 Flights from ~$214
Chicago main airports to arrive at
Chicago Midway International (MDW)
Consider Chicago Midway International for flights to Chicago, offering a convenient arrival option.
📍 ~15 km from Chicago city center (reachable by car)
💸 Flights from ~$214
Chicago Rockford International (RFD)
Chicago Rockford International is an alternative arrival airport for flights to the Chicago area.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$248
O Hare International (ORD)
O Hare International is a major airport for flights to Chicago, providing extensive connectivity.
📍 ~25 km from Chicago city center (reachable by car)
💸 Flights from ~$214
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
Consider MKE for its excellent proximity to Chicago and high-frequency flight options, despite potential traffic.
📍 ~135 km from Chicago (reachable by car or train)
💸 Flights from ~$338
South Bend International (SBN)
SBN is geographically the closest alternative to the Chicago area, offering easier security and parking.
📍 ~120 km from Chicago (reachable by car or train)
💸 Flights from ~$253
Gerald R. Ford International (GRR)
GRR is a major regional hub, a good alternative for travelers on the eastern side of the Chicago metro area.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$245
Dane County Regional (MSN)
MSN is a reliable regional airport with consistent service, less congested than major Chicago airports.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$262
Fort Wayne International (FWA)
FWA offers stable regional service and is an alternative for travelers in the southeastern Chicago suburbs.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$301
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from San Francisco to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From SFO
Elite
Nov 19
Chicago, United States
91% AI deal score
$1,632
$835
Save $797
From SFO
Elite
Nov 03
Chicago, United States
90% AI deal score
$1,502
$835
Save $667
From SFO
Elite
Nov 18
Chicago, United States
90% AI deal score
$1,519
$835
Save $684
From SFO
Elite
Nov 10
Chicago, United States
90% AI deal score
$1,510
$835
Save $675
From SFO
Elite
Nov 14
Chicago, United States
90% AI deal score
$1,505
$835
Save $670
From SFO
Elite
Nov 04
Chicago, United States
90% AI deal score
$1,502
$835
Save $667
From SFO
Elite
Dec 02
Chicago, United States
90% AI deal score
$1,662
$835
Save $827
From SFO
Elite
Nov 10
Chicago, United States
90% AI deal score
$1,546
$835
Save $711
From SFO
Elite
Nov 07
Chicago, United States
90% AI deal score
$1,547
$835
Save $712
From SFO
Elite
Nov 12
Chicago, United States
90% AI deal score
$1,546
$835
Save $711
From SFO
Elite
Nov 04
Chicago, United States
90% AI deal score
$1,548
$835
Save $713
From SFO
Elite
Sep 30
Chicago, United States
90% AI deal score
$1,598
$835
Save $763
From SFO
Elite
Nov 18
Chicago, United States
90% AI deal score
$1,643
$835
Save $808
From SFO
Elite
Nov 04
Chicago, United States
90% AI deal score
$1,520
$835
Save $685
From SFO
Elite
Nov 14
Chicago, United States
90% AI deal score
$1,539
$835
Save $704
From SFO
Elite
Nov 10
Chicago, United States
90% AI deal score
$1,542
$835
Save $707
From SFO
Elite
Nov 02
Chicago, United States
90% AI deal score
$1,521
$835
Save $686
From SFO
Elite
Nov 03
Chicago, United States
90% AI deal score
$1,520
$835
Save $685
From SFO
Elite
Nov 03
Chicago, United States
90% AI deal score
$1,537
$835
Save $702
From SFO
Elite
Nov 02
Chicago, United States
90% AI deal score
$1,522
$835
Save $687
From SFO
Elite
Nov 03
Chicago, United States
90% AI deal score
$1,544
$835
Save $709
From SFO
Elite
Nov 04
Chicago, United States
90% AI deal score
$1,536
$835
Save $701
From SFO
Elite
Nov 10
Chicago, United States
90% AI deal score
$1,543
$835
Save $708
From SFO
Elite
Nov 10
Chicago, United States
90% AI deal score
$1,644
$835
Save $809
From SFO
Elite
Nov 02
Chicago, United States
90% AI deal score
$1,537
$835
Save $702
From SFO
Elite
Nov 14
Chicago, United States
90% AI deal score
$1,630
$835
Save $795
From SFO
Elite
Nov 16
Chicago, United States
90% AI deal score
$1,542
$835
Save $707
From SFO
Elite
Nov 14
Chicago, United States
90% AI deal score
$1,512
$835
Save $677
From SFO
Elite
Nov 18
Chicago, United States
90% AI deal score
$1,508
$835
Save $673
From SFO
Elite
Oct 27
Chicago, United States
90% AI deal score
$1,534
$835
Save $699
From SFO
Elite
Oct 24
Chicago, United States
90% AI deal score
$1,539
$835
Save $704
From SFO
Elite
Dec 02
Chicago, United States
90% AI deal score
$1,559
$835
Save $724
From SFO
Elite
Oct 05
Chicago, United States
90% AI deal score
$1,551
$836
Save $715
From SFO
Elite
Aug 25
Chicago, United States
90% AI deal score
$1,542
$848
Save $694
From SFO
Elite
Nov 14
Chicago, United States
89% AI deal score
$1,518
$848
Save $670
From SFO
Elite
Nov 02
Chicago, United States
89% AI deal score
$1,501
$848
Save $653
From SFO
Elite
Nov 18
Chicago, United States
89% AI deal score
$1,517
$848
Save $669
From SFO
Elite
Nov 04
Chicago, United States
89% AI deal score
$1,504
$848
Save $656
From SFO
Elite
Nov 03
Chicago, United States
89% AI deal score
$1,501
$848
Save $653
From SFO
Elite
Nov 10
Chicago, United States
89% AI deal score
$1,510
$848
Save $662
From SFO
Elite
Nov 10
Chicago, United States
89% AI deal score
$1,330
$835
Save $495
From SFO
Elite
Nov 11
Chicago, United States
89% AI deal score
$1,329
$835
Save $494
From SFO
Elite
Nov 14
Chicago, United States
89% AI deal score
$1,343
$835
Save $508
From SFO
Elite
Aug 05
Chicago, United States
88% AI deal score
$1,264
$833
Save $431
From SFO
Elite
Aug 05
Chicago, United States
88% AI deal score
$1,271
$833
Save $438
From SFO
Elite
Nov 11
Chicago, United States
88% AI deal score
$1,230
$835
Save $395
From SFO
Elite
Nov 03
Chicago, United States
88% AI deal score
$1,242
$835
Save $407
From SFO
Elite
Nov 19
Chicago, United States
88% AI deal score
$1,241
$835
Save $406
From SFO
Elite
Nov 05
Chicago, United States
88% AI deal score
$1,259
$835
Save $424
From SFO
Elite
Nov 04
Chicago, United States
88% AI deal score
$1,244
$835
Save $409
From SFO
Elite
Nov 07
Chicago, United States
88% AI deal score
$1,295
$835
Save $460
From SFO
Elite
Nov 02
Chicago, United States
88% AI deal score
$1,242
$835
Save $407
From SFO
Elite
Jul 26
Chicago, United States
87% AI deal score
$1,237
$640
Save $597
From SFO
Elite
Jul 27
Chicago, United States
87% AI deal score
$1,254
$640
Save $614
From SFO
Elite
Aug 05
Chicago, United States
87% AI deal score
$1,219
$833
Save $386
From SFO
Elite
Nov 11
Chicago, United States
87% AI deal score
$1,224
$835
Save $389
From SFO
Elite
Nov 11
Chicago, United States
87% AI deal score
$1,224
$835
Save $389
From SFO
Elite
Nov 14
Chicago, United States
87% AI deal score
$1,224
$835
Save $389
From SFO
Elite
Nov 10
Chicago, United States
87% AI deal score
$1,224
$835
Save $389
From SFO
Elite
Nov 10
Chicago, United States
87% AI deal score
$1,224
$835
Save $389
From SFO
Elite
Nov 14
Chicago, United States
87% AI deal score
$1,224
$835
Save $389
From SFO
Elite
Nov 19
Chicago, United States
87% AI deal score
$1,224
$835
Save $389
From SFO
Elite
Nov 07
Chicago, United States
87% AI deal score
$1,224
$835
Save $389
From SFO
Elite
Nov 04
Chicago, United States
86% AI deal score
$1,638
$830
Save $808
From SFO
Elite
Jul 18
Chicago, United States
86% AI deal score
$1,437
$783
Save $654
From SFO
Elite
Jul 18
Chicago, United States
86% AI deal score
$1,426
$783
Save $643
From SFO
Elite
Jul 09
Chicago, United States
86% AI deal score
$2,201
$1,195
Save $1,006
From SFO
Elite
Jul 08
Chicago, United States
86% AI deal score
$2,201
$1,198
Save $1,003
From SFO
Elite
Jul 09
Chicago, United States
86% AI deal score
$2,193
$1,208
Save $985
From SFO
Elite
Jul 10
Chicago, United States
86% AI deal score
$2,207
$1,208
Save $999
From SFO
Elite
Jul 21
Chicago, United States
86% AI deal score
$2,241
$1,208
Save $1,033
From SFO
Elite
Jul 27
Chicago, United States
86% AI deal score
$2,201
$1,208
Save $993
From SFO
Elite
Jun 17
Chicago, United States
85% AI deal score
$1,994
$1,101
Save $893
From SFO
Elite
Jul 22
Chicago, United States
85% AI deal score
$1,427
$865
Save $562
From SFO
Elite
Aug 07
Chicago, United States
85% AI deal score
$1,599
$901
Save $698
From SFO
Elite
Jul 20
Chicago, United States
85% AI deal score
$1,457
$803
Save $654
From SFO
Elite
Jul 20
Chicago, United States
85% AI deal score
$1,453
$803
Save $650
From SFO
Elite
Jul 21
Chicago, United States
85% AI deal score
$1,457
$803
Save $654
From SFO
Elite
Jul 18
Chicago, United States
85% AI deal score
$1,453
$820
Save $633
From SFO
Elite
Jul 18
Chicago, United States
85% AI deal score
$1,427
$820
Save $607
From SFO
Elite
Jul 18
Chicago, United States
85% AI deal score
$1,369
$820
Save $549
From SFO
Elite
Jul 18
Chicago, United States
85% AI deal score
$1,369
$820
Save $549
From SFO
Elite
Jul 19
Chicago, United States
85% AI deal score
$1,369
$820
Save $549
From SFO
Elite
Jul 20
Chicago, United States
85% AI deal score
$1,427
$820
Save $607
From SFO
Elite
Jul 21
Chicago, United States
85% AI deal score
$1,426
$820
Save $606
From SFO
Elite
Jul 24
Chicago, United States
85% AI deal score
$1,457
$820
Save $637
From SFO
Elite
Nov 13
Chicago, United States
85% AI deal score
$2,261
$1,198
Save $1,063
From SFO
Elite
Aug 17
Chicago, United States
84% AI deal score
$1,222
$780
Save $442
From SFO
Elite
Aug 29
Chicago, United States
84% AI deal score
$1,261
$783
Save $478
From SFO
Elite
Aug 28
Chicago, United States
84% AI deal score
$1,273
$783
Save $490
From SFO
Elite
Jul 19
Chicago, United States
84% AI deal score
$1,453
$839
Save $614
From SFO
Elite
Jul 19
Chicago, United States
84% AI deal score
$1,437
$839
Save $598
From SFO
Elite
Jul 20
Chicago, United States
84% AI deal score
$1,437
$839
Save $598
From SFO
Elite
Jul 20
Chicago, United States
84% AI deal score
$1,426
$839
Save $587
From SFO
Elite
Jul 21
Chicago, United States
84% AI deal score
$1,436
$839
Save $597
From SFO
Elite
Jul 22
Chicago, United States
84% AI deal score
$1,436
$857
Save $579
From SFO
Elite
Jul 22
Chicago, United States
84% AI deal score
$1,457
$874
Save $583
From SFO
Elite
Jul 22
Chicago, United States
84% AI deal score
$1,453
$874
Save $579
From SFO
Elite
Jul 19
Chicago, United States
84% AI deal score
$1,457
$875
Save $582
From SFO
Elite
Jun 19
Chicago, United States
84% AI deal score
$1,651
$1,058
Save $593