Cheap Flights from Oakland to Chicago
Browse current best options from Oakland. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Oakland
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 Oakland to Chicago
Explore current cheapest deals departing from Oakland to Chicago
Round trip
Sort by: Cheapest
August 18 - August 22
OAK - Chicago
$396
$253
Round trip
August 13 - August 18
OAK - Chicago
$351
$262
Round trip
August 13 - August 20
OAK - Chicago
$340
$262
Round trip
August 13 - August 22
OAK - Chicago
$329
$262
Round trip
September 23 - September 26
OAK - Chicago
$273
$262
Round trip
September 24 - September 29
OAK - Chicago
$342
$262
Round trip
August 20 - August 25
OAK - Chicago
$352
$263
Round trip
August 20 - August 29
OAK - Chicago
$330
$263
Round trip
August 17 - August 19
OAK - Chicago
$358
$263
Round trip
August 27 - August 29
OAK - Chicago
$358
$263
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 Oakland to Chicago
How much is a round trip from Oakland to Chicago
Regular price: $253 - $438
Prices for flights from Oakland to Chicago are currently within the regular range.
The regular price range for flights from Oakland to Chicago is between $253 and $438. The current lowest deal is $335 on Kayak for travel from Jul 21-Jul 29.
now $335
Low $253
High $438
The cheapest time to fly from Oakland to Chicago
The cheapest month to fly from OAK to CHI is February, with a median price of $178. The most expensive month is March, with a median price of $752. Prices are generally lower from February to December.
February
Flights from $178
March
Flights from $752
Direct flights from Oakland to Chicago
Southwest Airlines
Last-minute flights going from Oakland to Chicago
Wed, Jul 8
OAK - Chicago
Oakland (OAK) - Chicago (MDW)
Southwest Airlines
$359
$274
One-way
Wed, Jul 8
OAK - Chicago
Oakland (OAK) - Chicago (ORD)
Alaska Airlines, Inc.
$305
$299
One-way
Sat, Jul 11
OAK - Chicago
Oakland (OAK) - Chicago (ORD)
Alaska Airlines, Inc.
$358
$311
One-way
Mon, Jul 13
OAK - Chicago
Oakland (OAK) - Chicago (ORD)
Alaska Airlines, Inc.
$353
$298
One-way
Wed, Jul 15
OAK - Chicago
Oakland (OAK) - Chicago (MDW)
Southwest Airlines
$383
$273
One-way
Wed, Jul 15
OAK - Chicago
Oakland (OAK) - Chicago (MDW)
Southwest Airlines
$391
$310
One-way
Biggest price drops on these dates for flights from Oakland to Chicago
Nov 18 - Nov 21
$500 → $355
29%
Nov 17 - Nov 18
$499 → $355
29%
Aug 18 - Aug 22
$396 → $253
36%
Nov 26 - Dec 2
$496 → $355
28%
Popular Airports to fly from Oakland to Chicago
Oakland - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from Oakland to Chicago are below the typical level at $253.
📅 Best time to fly
February is historically cheapest at $178
Historically, February is the cheapest month to fly, with a median price of $178.
⏱️ Flight duration
Connecting flights average 18h 52m
Flights from Oakland to Chicago typically involve connections, with a median duration of 18h 52m.
✈️ Airlines & availability
Connecting flights are frequent
Connecting flights are frequent, with over 1 deal per day historically available from Oakland to Chicago.
🏆 Airline highlight
Southwest Airlines offers connecting flights
Southwest Airlines offers connecting flights from Oakland to Chicago, with recent deals found for $253.
🎯 Booking tip
Book during February to December for lower prices
Historically, flights from February to December offer lower prices for this route.
Oakland main airports to depart from
Oakland International (OAK)
Oakland International is a good option for flights from Oakland to Chicago, offering competitive prices.
📍 ~10 km from city center (reachable by car)
💸 Flights from ~$253
Chicago main airports to arrive at
Chicago Midway International (MDW)
Chicago Midway International Airport is a good choice for flights from Oakland to Chicago, with prices from $253.
📍 ~15 km from Chicago city center (reachable by car, train, bus)
💸 Flights from ~$253
Chicago Rockford International (RFD)
Chicago Rockford International Airport is an alternative arrival option for flights from Oakland to Chicago.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$881
O Hare International (ORD)
O Hare International Airport is a major hub for flights from Oakland to Chicago, with prices from $262.
📍 ~25 km from Chicago city center (reachable by car, train, bus)
💸 Flights from ~$262
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by rail; travel time can be affected by heavy traffic).
💸 Flights from ~$368
South Bend International (SBN)
South Bend International is geographically the closest alternative to Chicago, with easier security and parking.
📍 ~120 km from Chicago (reachable by rail).
💸 Flights from ~$552
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub offering a wide range of cabin classes.
📍 ~250 km from Chicago (requires a significant drive).
💸 Flights from ~$313
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service and less congestion than major hubs.
📍 ~200 km from Chicago.
💸 Flights from ~$556
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service and is an alternative for southeastern Chicago suburbs.
📍 ~240 km from Chicago (significant distance and limited flight frequency).
💸 Flights from ~$848
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Oakland to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From OAK
Elite
Nov 11
Chicago, United States
91% AI deal score
$2,084
$991
Save $1,093
From OAK
Elite
Nov 11
Chicago, United States
91% AI deal score
$2,021
$1,014
Save $1,007
From OAK
Elite
Sep 13
Chicago, United States
91% AI deal score
$2,170
$1,019
Save $1,151
From OAK
Elite
Sep 13
Chicago, United States
91% AI deal score
$2,212
$1,019
Save $1,193
From OAK
Elite
Sep 11
Chicago, United States
91% AI deal score
$2,136
$1,034
Save $1,102
From OAK
Elite
Sep 11
Chicago, United States
91% AI deal score
$2,201
$1,034
Save $1,167
From OAK
Elite
Oct 03
Chicago, United States
91% AI deal score
$2,123
$1,043
Save $1,080
From OAK
Elite
Oct 03
Chicago, United States
91% AI deal score
$2,101
$1,043
Save $1,058
From OAK
Elite
Aug 13
Chicago, United States
91% AI deal score
$2,192
$1,050
Save $1,142
From OAK
Elite
Oct 02
Chicago, United States
91% AI deal score
$2,107
$1,053
Save $1,054
From OAK
Elite
Oct 02
Chicago, United States
91% AI deal score
$2,110
$1,053
Save $1,057
From OAK
Elite
Aug 11
Chicago, United States
91% AI deal score
$2,256
$1,068
Save $1,188
From OAK
Elite
Aug 12
Chicago, United States
91% AI deal score
$2,261
$1,068
Save $1,193
From OAK
Elite
Aug 05
Chicago, United States
91% AI deal score
$2,204
$1,068
Save $1,136
From OAK
Elite
Aug 27
Chicago, United States
91% AI deal score
$2,300
$1,083
Save $1,217
From OAK
Elite
Aug 03
Chicago, United States
91% AI deal score
$2,306
$1,115
Save $1,191
From OAK
Elite
Nov 11
Chicago, United States
90% AI deal score
$2,107
$1,039
Save $1,068
From OAK
Elite
Nov 11
Chicago, United States
90% AI deal score
$2,021
$1,050
Save $971
From OAK
Elite
Nov 11
Chicago, United States
90% AI deal score
$2,028
$1,050
Save $978
From OAK
Elite
Nov 09
Chicago, United States
90% AI deal score
$2,029
$1,068
Save $961
From OAK
Elite
Nov 22
Chicago, United States
89% AI deal score
$2,051
$1,133
Save $918
From OAK
Elite
Jul 28
Chicago, United States
89% AI deal score
$1,890
$1,043
Save $847
From OAK
Elite
Dec 09
Chicago, United States
89% AI deal score
$2,058
$1,114
Save $944
From OAK
Elite
Dec 08
Chicago, United States
89% AI deal score
$2,047
$1,114
Save $933
From OAK
Elite
Jul 08
Chicago, United States
88% AI deal score
$2,090
$1,176
Save $914
From OAK
Elite
Nov 03
Chicago, United States
88% AI deal score
$1,714
$1,039
Save $675
From OAK
Elite
Nov 03
Chicago, United States
88% AI deal score
$1,700
$1,039
Save $661
From OAK
Elite
Dec 07
Chicago, United States
88% AI deal score
$1,999
$1,150
Save $849
From OAK
Elite
Dec 10
Chicago, United States
88% AI deal score
$2,062
$1,150
Save $912
From OAK
Elite
Oct 06
Chicago, United States
87% AI deal score
$2,204
$985
Save $1,219
From OAK
Elite
Aug 12
Chicago, United States
87% AI deal score
$2,192
$1,014
Save $1,178
From OAK
Elite
Aug 11
Chicago, United States
87% AI deal score
$2,188
$1,014
Save $1,174
From OAK
Elite
Aug 31
Chicago, United States
87% AI deal score
$2,211
$1,019
Save $1,192
From OAK
Elite
Aug 31
Chicago, United States
87% AI deal score
$2,204
$1,019
Save $1,185
From OAK
Elite
Aug 31
Chicago, United States
87% AI deal score
$2,286
$1,019
Save $1,267
From OAK
Elite
Aug 31
Chicago, United States
87% AI deal score
$2,326
$1,043
Save $1,283
From OAK
Elite
Aug 05
Chicago, United States
87% AI deal score
$2,423
$1,079
Save $1,344
From OAK
Elite
Oct 14
Chicago, United States
87% AI deal score
$1,619
$1,019
Save $600
From OAK
Elite
Oct 17
Chicago, United States
87% AI deal score
$1,662
$1,043
Save $619
From OAK
Elite
Oct 17
Chicago, United States
87% AI deal score
$1,666
$1,063
Save $603
From OAK
Elite
Nov 18
Chicago, United States
87% AI deal score
$1,712
$1,068
Save $644
From OAK
Elite
Aug 27
Chicago, United States
87% AI deal score
$2,046
$1,181
Save $865
From OAK
Elite
Aug 05
Chicago, United States
86% AI deal score
$2,184
$1,038
Save $1,146
From OAK
Elite
Aug 12
Chicago, United States
86% AI deal score
$2,225
$1,038
Save $1,187
From OAK
Elite
Aug 11
Chicago, United States
86% AI deal score
$2,213
$1,038
Save $1,175
From OAK
Elite
Aug 11
Chicago, United States
86% AI deal score
$2,192
$1,038
Save $1,154
From OAK
Elite
Aug 12
Chicago, United States
86% AI deal score
$2,192
$1,038
Save $1,154
From OAK
Elite
Aug 12
Chicago, United States
86% AI deal score
$2,432
$1,212
Save $1,220
From OAK
Elite
Jul 22
Chicago, United States
86% AI deal score
$2,077
$1,283
Save $794
From OAK
Elite
Jul 11
Chicago, United States
86% AI deal score
$2,161
$1,313
Save $848
From OAK
Elite
Jun 17
Chicago, United States
86% AI deal score
$2,754
$1,389
Save $1,365
From OAK
Elite
Oct 14
Chicago, United States
86% AI deal score
$1,580
$1,034
Save $546
From OAK
Elite
Sep 21
Chicago, United States
86% AI deal score
$1,582
$1,034
Save $548
From OAK
Elite
Oct 14
Chicago, United States
86% AI deal score
$1,569
$1,039
Save $530
From OAK
Elite
Oct 14
Chicago, United States
86% AI deal score
$1,569
$1,039
Save $530
From OAK
Elite
Oct 14
Chicago, United States
86% AI deal score
$1,575
$1,039
Save $536
From OAK
Elite
Nov 18
Chicago, United States
86% AI deal score
$1,594
$1,050
Save $544
From OAK
Elite
Sep 21
Chicago, United States
86% AI deal score
$1,582
$1,053
Save $529
From OAK
Elite
Nov 03
Chicago, United States
86% AI deal score
$1,596
$1,068
Save $528
From OAK
Elite
Nov 18
Chicago, United States
86% AI deal score
$1,627
$1,068
Save $559
From OAK
Elite
Dec 02
Chicago, United States
86% AI deal score
$1,710
$1,114
Save $596
From OAK
Elite
Aug 07
Chicago, United States
86% AI deal score
$2,145
$1,268
Save $877
From OAK
Elite
Aug 02
Chicago, United States
85% AI deal score
$2,589
$1,303
Save $1,286
From OAK
Elite
Oct 01
Chicago, United States
85% AI deal score
$1,578
$1,053
Save $525
From OAK
Elite
Oct 04
Chicago, United States
85% AI deal score
$1,581
$1,053
Save $528
From OAK
Elite
Aug 12
Chicago, United States
85% AI deal score
$2,073
$1,079
Save $994
From OAK
Elite
Dec 05
Chicago, United States
85% AI deal score
$1,695
$1,150
Save $545
From OAK
Elite
Nov 26
Chicago, United States
85% AI deal score
$1,636
$1,150
Save $486
From OAK
Elite
Sep 04
Chicago, United States
85% AI deal score
$1,861
$1,231
Save $630
From OAK
Elite
Nov 21
Chicago, United States
84% AI deal score
$2,071
$1,171
Save $900
From OAK
Elite
Sep 07
Chicago, United States
84% AI deal score
$1,497
$1,034
Save $463
From OAK
Elite
Sep 06
Chicago, United States
84% AI deal score
$1,502
$1,034
Save $468
From OAK
Elite
Sep 06
Chicago, United States
84% AI deal score
$1,502
$1,053
Save $449
From OAK
Elite
Sep 07
Chicago, United States
84% AI deal score
$1,512
$1,053
Save $459
From OAK
Elite
Nov 24
Chicago, United States
84% AI deal score
$1,607
$1,150
Save $457
From OAK
Elite
Nov 22
Chicago, United States
84% AI deal score
$1,607
$1,168
Save $439
From OAK
Elite
Aug 11
Chicago, United States
84% AI deal score
$1,934
$1,302
Save $632
From OAK
Elite
Jun 20
Chicago, United States
84% AI deal score
$2,062
$1,398
Save $664
From OAK
Elite
Jul 07
Chicago, United States
83% AI deal score
$2,162
$1,278
Save $884
From OAK
Elite
Jul 20
Chicago, United States
83% AI deal score
$2,296
$1,302
Save $994
From OAK
Elite
Aug 05
Chicago, United States
83% AI deal score
$1,644
$1,178
Save $466
From OAK
Elite
Jun 20
Chicago, United States
82% AI deal score
$2,644
$1,581
Save $1,063
From OAK
Elite
Jun 18
Chicago, United States
82% AI deal score
$2,631
$1,858
Save $773
From OAK
Elite
Jul 20
Chicago, United States
82% AI deal score
$1,918
$1,190
Save $728
From OAK
Elite
Jul 16
Chicago, United States
82% AI deal score
$1,761
$1,292
Save $469
From OAK
Elite
Jun 25
Chicago, United States
81% AI deal score
$2,474
$1,496
Save $978
From OAK
Elite
Jun 19
Chicago, United States
80% AI deal score
$2,629
$1,708
Save $921
From OAK
Elite
Aug 21
Chicago, United States
80% AI deal score
$2,002
$1,297
Save $705
From OAK
Elite
Jul 23
Chicago, United States
78% AI deal score
$2,268
$1,558
Save $710
From OAK
Elite
Nov 21
Chicago, United States
78% AI deal score
$1,761
$1,347
Save $414
From OAK
Elite
Oct 21
Chicago, United States
78% AI deal score
$1,782
$1,369
Save $413
From OAK
Elite
Nov 30
Chicago, United States
77% AI deal score
$1,693
$1,344
Save $349
From OAK
Elite
Jun 17
Chicago, United States
73% AI deal score
$2,665
$2,451
Save $214
From OAK
Elite
Jul 27
Chicago, United States
72% AI deal score
$1,819
$1,471
Save $348
From OAK
Elite
Aug 02
Chicago, United States
67% AI deal score
$2,223
$2,149
Save $74
From OAK
Elite
Jul 11
Chicago, United States
66% AI deal score
$1,551
From OAK
Elite
Jul 18
Chicago, United States
48% AI deal score
$1,581
From OAK
Elite
Jul 14
Chicago, United States
46% AI deal score
$1,889
From OAK
Elite
Jul 07
Chicago, United States
45% AI deal score
$1,889
From OAK
Elite
Jul 01
Chicago, United States
45% AI deal score
$2,084