Cheap Flights from Oakland to Chicago
We've found these cheap flights for you. You can book one-way or return flight tickets.
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Flight deals from Oakland to Chicago
We've found these cheap flights for you. You can book one-way or return flight tickets.
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Round-trip
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One way
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Cheapest nonstop
OAK 05:054h 10mNonstopMDW 11:15Oakland - Chicago | Mon, Apr 21 | Southwest Airlines
MDW 16:554h 35mNonstopOAK 19:30Chicago - Oakland | Tue, Apr 29 | Southwest AirlinesNZD 353 NZD 55236% OFF36% OFFNZD 552 NZD 353 -
OAK 05:554h 10mNonstopMDW 12:05Oakland - Chicago | Sun, Apr 27 | Southwest Airlines
MDW 16:554h 35mNonstopOAK 19:30Chicago - Oakland | Sat, May 3 | Southwest AirlinesNZD 356 NZD 55236% OFF36% OFFNZD 552 NZD 356
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OAK 12:1115h 12m1 stopsMDW 05:23Oakland - Chicago | Wed, Apr 2 | Spirit Airlines
MDW 20:5023h 5m1 stopsOAK 17:55Chicago - Oakland | Thu, Apr 3 | Frontier AirlinesNZD 320 NZD 55242% OFF42% OFFNZD 552 NZD 320 -
OAK 07:3119h 23m1 stopsORD 04:54Oakland - Chicago | Thu, Apr 3 | Spirit Airlines
ORD 20:0123h 54m1 stopsOAK 17:55Chicago - Oakland | Fri, Apr 4 | Frontier AirlinesNZD 35037% OFFNZD 552 NZD 350
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OAK 06:438h 10m1 stopsORD 16:53Oakland - Chicago | Tue, Apr 15 | Hawaiian Airlines
ORD 15:4410h1 stopsOAK 23:44Chicago - Oakland | Tue, Apr 22 | Hawaiian AirlinesNZD 36833% OFFNZD 552 NZD 368 -
OAK 06:438h 10m1 stopsORD 16:53Oakland - Chicago | Tue, Apr 15 | Alaska Airlines
ORD 17:567h 48m1 stopsOAK 23:44Chicago - Oakland | Tue, Apr 22 | Alaska AirlinesNZD 37432% OFFNZD 552 NZD 374 -
OAK 06:054h 10mNonstopMDW 12:15Oakland - Chicago | Sat, Apr 19 | Southwest Airlines
ORD 17:567h 48m1 stopsOAK 23:44Chicago - Oakland | Sat, Apr 26 | Hawaiian AirlinesNZD 39328% OFFNZD 552 NZD 393
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OAK 07:008h1 stopsORD 17:00Oakland - Chicago | Sat, Apr 26 | Alaska Airlines
MDW 16:554h 35mNonstopOAK 19:30Chicago - Oakland | Sat, May 3 | Southwest AirlinesNZD 39728% OFFNZD 552 NZD 397
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OAK 12:459h 14m1 stopsORD 23:59Oakland - Chicago | Wed, Apr 23 | Alaska Airlines
ORD 17:567h 48m1 stopsOAK 23:44Chicago - Oakland | Wed, Apr 30 | Alaska AirlinesNZD 40327% OFFNZD 552 NZD 403
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OAK 07:008h1 stopsORD 17:00Oakland - Chicago | Tue, Apr 29 | Alaska Airlines
ORD 06:008h 1m1 stopsOAK 12:01Chicago - Oakland | Tue, May 6 | Alaska AirlinesNZD 40327% OFFNZD 552 NZD 403
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OAK 13:0017h 25m1 stopsCHI Invalid DateOakland - Chicago | Sun, Mar 30 | Normal Airline
CHI 15:006hNonstopOAK 16:00Chicago - Oakland | Tue, Apr 1 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
OAK 05:054h 10mNonstopMDW 11:15Oakland - Chicago | Mon, May 5 | Southwest AirlinesNZD 194 NZD 31438% OFF38% OFFNZD 314 NZD 194
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OAK 05:504h 10mNonstopMDW 12:00Oakland - Chicago | Wed, Apr 9 | Southwest AirlinesNZD 229 NZD 31427% OFF27% OFFNZD 314 NZD 229
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OAK 12:1115h 12m1 stopsMDW 05:23Oakland - Chicago | Wed, Apr 2 | Spirit AirlinesNZD 129 NZD 31459% OFF59% OFFNZD 314 NZD 129
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OAK 12:1116h 31m1 stopsORD 06:42Oakland - Chicago | Tue, Apr 1 | Spirit AirlinesNZD 13956% OFFNZD 314 NZD 139
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OAK 06:438h 10m1 stopsORD 16:53Oakland - Chicago | Tue, Apr 15 | Hawaiian AirlinesNZD 17046% OFFNZD 314 NZD 170
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OAK 05:3523h 7m1 stopsORD 06:42Oakland - Chicago | Tue, Apr 1 | Southwest AirlinesNZD 17145% OFFNZD 314 NZD 171
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OAK 06:439h 12m1 stopsORD 17:55Oakland - Chicago | Tue, Apr 15 | Alaska AirlinesNZD 17345% OFFNZD 314 NZD 173
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OAK 07:009h 1m1 stopsORD 18:01Oakland - Chicago | Tue, Apr 29 | Alaska AirlinesNZD 18342% OFFNZD 314 NZD 183
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OAK 18:2910h 4m1 stopsORD 06:33Oakland - Chicago | Wed, Apr 9 | Spirit AirlinesNZD 18641% OFFNZD 314 NZD 186
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OAK 08:1518h 55m1 stopsORD 05:10Oakland - Chicago | Mon, May 5 | Southwest AirlinesNZD 19239% OFFNZD 314 NZD 192
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OAK 18:5516h 44m1 stopsORD 13:39Oakland - Chicago | Mon, Mar 31 | Spirit AirlinesNZD 19338% OFFNZD 314 NZD 193
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OAK 18:2910h 4m1 stopsORD 06:33Oakland - Chicago | Wed, Apr 16 | Spirit AirlinesNZD 19538% OFFNZD 314 NZD 195
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OAK 13:0017h 25m1 stopsCHI Invalid DateOakland - Chicago | Sun, Mar 30 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
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Airlines Flying from Oakland to Chicago
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FAQ
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When are flight tickets from Oakland (OAK) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Oakland to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much do flights from Oakland (OAK) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around NZD 748. -
How long does it take to fly from Oakland (OAK) to Chicago (CHI) and what is the distance?
It takes around 5 hours 37 minutes to fly from Oakland (OAK) to Chicago (CHI). -
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare Intl. Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
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What are the most popular airlines that fly from Oakland (OAK) to Chicago (CHI)?
Airlines with flights from Oakland (OAK) to Chicago (CHI): Southwest Airlines.
How to find a cheap flight from Oakland to Chicago
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Oakland to Chicago. Book your flights at the right time and save more.
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Check One-way Fares
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Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
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Flight Information from Oakland to Chicago
| Cheapest one-way flight price | NZD 128 |
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| Cheapest round-trip ticket price | NZD 352 |
| Off-season for travel | April |
| Peak season for travel | December |
| Flight distance | 2,969.56 km |
| Average flight time | 5 hours 37 minutes |
| Popular airline | Alaska Airlines |