Oakland → Chicago

Nonstop flights

• WNSouthwest AirlinesLCC

Best places to connect

22 one-stop options, sorted by estimated flying time. Tap one to see the airlines on each leg and booking links.

• DENvia Denver≈ 4h 29m
  Fastest · detour 0%
  Same airline: WNLCC option
  OAK→DENWN

  DEN→MDWWN F9
  See itinerary
• SLCvia Salt Lake City≈ 4h 30m
  +1m vs fastest · detour 0%
  Same airline: WNLCC option
  OAK→SLCWN

  SLC→MDWWN
  See itinerary
• LASvia Las Vegas≈ 4h 38m
  +9m vs fastest · detour 5%
  Same airline: WNLCC option
  OAK→LASWN F9

  LAS→MDWWN
  See itinerary
• BOIvia Boise≈ 4h 42m
  +13m vs fastest · detour 6%
  Same airline: WNLCC option
  OAK→BOIWN

  BOI→MDWWN
  See itinerary
• ABQvia Albuquerque≈ 4h 48m
  +19m vs fastest · detour 9%
  Same airline: WNLCC option
  OAK→ABQWN

  ABQ→MDWWN
  See itinerary
• BURvia Burbank≈ 4h 54m
  +25m vs fastest · detour 12%
  Same airline: WNLCC option
  OAK→BURWN

  BUR→MDWWN
  See itinerary
• ONTvia Ontario≈ 4h 54m
  +25m vs fastest · detour 12%
  Same airline: WNLCC option
  OAK→ONTWN

  ONT→MDWWN
  See itinerary
• PSPvia Palm Springs≈ 4h 56m
  +27m vs fastest · detour 13%
  Same airline: WNLCC option
  OAK→PSPWN

  PSP→MDWWN
  See itinerary
• LAXvia Los Angeles≈ 4h 56m
  +27m vs fastest · detour 13%
  Same airline: WNLCC option
  OAK→LAXWN

  LAX→MDWWN
  See itinerary
• PHXvia Phoenix≈ 4h 57m
  +28m vs fastest · detour 13%
  Same airline: WNLCC option
  OAK→PHXWN

  PHX→MDWF9 WN
  See itinerary
• LGBvia Long Beach≈ 4h 57m
  +28m vs fastest · detour 14%
  Same airline: WNLCC option
  OAK→LGBWN

  LGB→MDWWN
  See itinerary
• SANvia San Diego≈ 5h 7m
  +38m vs fastest · detour 18%
  Same airline: WNLCC option
  OAK→SANWN AS

  SAN→MDWWN
  See itinerary
• GEGvia Spokane≈ 5h 13m
  +44m vs fastest · detour 21%
  Same airline: WNLCC option
  OAK→GEGWN

  GEG→MDWWN
  See itinerary
• DALvia Dallas≈ 5h 16m
  +47m vs fastest · detour 23%
  Same airline: WNLCC option
  OAK→DALWN

  DAL→MDWWN
  See itinerary
• PDXvia Portland≈ 5h 20m
  +51m vs fastest · detour 25%
  Same airline: WNLCC option
  OAK→PDXWN AS

  PDX→MDWWN
  See itinerary
• SEAvia Seattle≈ 5h 32m
  +1h 3m vs fastest · detour 30%
  Same airline: WNLCC option
  OAK→SEAWN AS

  SEA→MDWWN
  See itinerary
• AUSvia Austin≈ 5h 40m
  +1h 11m vs fastest · detour 34%
  Same airline: WNLCC option
  OAK→AUSWN

  AUS→MDWWN
  See itinerary
• HOUvia Houston≈ 5h 53m
  +1h 24m vs fastest · detour 40%
  Same airline: WNLCC option
  OAK→HOUWN

  HOU→MDWWN
  See itinerary
• SJDvia San José del Cabo≈ 6h 47m
  +2h 18m vs fastest · detour 66%
  Same airline: WNLCC option
  OAK→SJDWN

  SJD→MDWWN
  See itinerary
• BJXvia Silao≈ 7h 19m
  +2h 50m vs fastest · detour 81%
  Same airline: Y4LCC option
  OAK→BJXY4

  BJX→MDWY4
  See itinerary
• GDLvia Guadalajara≈ 7h 22m
  +2h 53m vs fastest · detour 83%
  Same airline: Y4LCC option
  OAK→GDLY4

  GDL→MDWY4
  See itinerary
• MLMvia Morelia≈ 7h 34m
  +3h 5m vs fastest · detour 89%
  Same airline: Y4LCC option
  OAK→MLMY4

  MLM→MDWY4
  See itinerary