Find cheap flights from Oakland to Chicago O'Hare Airport

OAK - ORD

Find cheap flights from Oakland to Chicago O'Hare Airport

Round-trip
Economy
Oakland (OAK)
Chicago O'Hare Intl
Fri 10/30
Fri 11/6
Any month
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Good to know

Low season

July Best time to beat the crowds with an average 42% drop in price.

High season

December Most popular time to fly with an average 38% increase in price.

Average price of a round-trip

$207 (avg. price over the last 2 weeks)

Good deal for a round-trip

$172 or less

When to book flights from Oakland to Chicago O'Hare Intl

Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $155 or less.
  • The cheapest flight from Oakland to Chicago O'Hare Airport was found 48 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is July.
  • Morning departure is around 16% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Oakland to Chicago O'Hare Airport flights

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What’s the cheapest day of the week to fly Oakland to Chicago O'Hare Airport?

How does KAYAK find such low prices on flights from Oakland to Chicago O'Hare Airport?

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What is the Hacker Fare option on flights from Oakland to Chicago O'Hare Airport?

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Top airline flying Oakland to Chicago O'Hare Intl

Scores according to KAYAK customer reviews

5.6
Spirit Airlines
Overall score based on 61,395 reviews
6.1
Boarding
5.4
Comfort
6.5
Crew
4.6
Entertainment
4.7
Food
Airline reviews

Pros: "Clean and simple"
Cons: "To pay for absolutely everything"

Pros: "Nothing"
Cons: "Everything"

Cons: "Spirit charges for everything, including stuff that doesn't cost them, like choosing a seat."

Pros: "I like how fast I boarded."
Cons: "The limited seating room and how long I waited to retrieve my luggage."

Pros: "Not worth my time"
Cons: "Not worth my time"

Pros: "Spirit Airlines did perfectly into a specific niche of travelers. I'm glad that they operate in this space."

Cons: "I will never fly this airline again."

Pros: "On time ....good crews etc..."
Cons: "Baggages very very expensive $50 ea...back bag $30... more than shipping rates ($2.00/lb)."

Cons: "learning upon arriving at the airport that I had to pay $55 each way for a checked bag. Would prefer that Kayak warn buyers that they are likely to pay over $100 for a single bag other than a purse."

Cons: "We did not received a complimentary snack. I was very hungry and needed to take my medication with water. I didn't traveled with credit cards and I didn't had enough cash to buy a water or soda."

Pros: "They charge me more money for baggage $22 more than regular charge Would you please give me their phone#"

Cons: "Spirit Airlines charges for your carry on luggage. So the cheap ticket prices are good if you don't bring any luggage. Nothing is complimentary. The seats are totally cramped. I'm short and wasn't very comfortable. I have no idea how tall people handle it. I will not be choosing Spirit Airlines in the future."

Cons: "My wallet was stolen in San Francisco so I called to change my flight to a time when a duplicate ID was sent through the mail from my home state's dmv. Instead of transfering the flight i already paid for the customer service representative forced me to purchase a completely new one way ticket back to o hare, in addition to a flight change fee. The representive kept trying to push me off the line when I asked what the new charges were and why no offset any of the costs I had paid for for my intial return including the ticket price, fare difference, baggage purchases, and seat selection was offered. After trying to hang up on me several times she finally agreed to let me switch my flight, for $200 more on top of the ticket i had already bought, bringing my total expenses for my trip home well above $600. Later, through email, I found that she had not in fact switched my flight, but forces me to buy another flight altogether. After this transaction went through she started asking me about my personal information, social security card number, income, my career. When I asked her why She was doing this she said that she was signing me up for a spirit airlines credit card. I was astonished, and before I could even ask why she was doing this without my consent she thanked me for my business and shrewdly hung up the phone."

Pros: "Very smooth flight."
Cons: "Unclear size directions for fees."

Pros: "PRETTY DISGUSTED WIITH THEM"
Cons: "Internet Registration and phone service is down right Sleazy Those not used to used to using the internet can be RIPPED OFF for 100.00 of dollars with there graded fees.Run like a casino."

Pros: "Flight on time"
Cons: "No complimentary drink like water even 4oz $55 fee for carry on is ridiculous Seats don't recline give me back pain and stiff neck"

Pros: "The website was down the night before my flight. The airlines wanted to charge me a #10. fee to print it anyway. The wait in line was 45 minutes to get a ticket. 45 dollars to carry on a bag. 15 to request a seat. What other business could be run like that and survive?"

Pros: "Cheap even with paying to check a bad and choosing a seat."
Cons: "No food or drinks. Seats did not recline."

Pros: "Good accommodating staff"
Cons: "Heavy charges for luggage Improvements in website"

Pros: "The flight crew were very friendly and attentive"
Cons: "I wish they at least gave free water, seats are very rigid"

Pros: "Not much."
Cons: "You nickel and dime for every aspect of the experience, from checking in, selecting seats, carrying on my bag, getting a beverage. Then I get to my seat, which for some reason has a folding trey table within the seat, making the seat smaller than the others. I'm a tall man, this was the most uncomfortable flight I've ever flown on. I was squeezed into a seat that didn't fit. I won't be flying with you again, and will suggest my friends and family not as well. You charged $55 for a carry-on bag? What a con!"

Pros: "Cheap. It Was better than my return flight when they didn't allow me to board the plane."
Cons: "4 hour flight on the worst seat on the plane."

Pros: "Flight was on time and boarding process is quick and efficient"
Cons: "Extra charges for everything! Paying for carry-on bags, assigning seats, drinks/snacks, etc. No inflight entertainment. No wifi option etc. At the end, you pay the same (or more) for the flight that lags traditional services."

Cons: "Flight took off late. Had to taxi in Chicago for 40 min."

Cons: "Late departure, late arrivel, lost luggage"

Pros: "The flight was on schedule, no tricks or money extortion. No comfort is expected for a deeply discounted fare. It was as promised."

Pros: "Staff seemed nice."
Cons: "The seats were uncomfortable and didn't recline."

Pros: "We did reach our destination on time."
Cons: "The cheesiest plane I have ever been on. The creeking is unnerving. The cost of a carry on, INSANE! Rate the food and entertainment- all fees! This airline is a total rip off. I tell everyone how awful it is."

Cons: "My flight was delayed over an hour with no notification. The seats were, if possible, smaller than normal. My return flight was delayed 5 hours, again without prior notification and then cancelled after waiting in the airport for 5 hours. Terrible. Not worth the money saved as you pay for it in seat reservations and back checks. There isn't even free water!"

Pros: "Nothing."
Cons: "CARRY-ONS cost money. They cost more money if you don't buy them ahead of time. It costs extra to CHECK IN WITH AN AGENT. The airline is not upfront about any of this. These charges supposedly keep the cost of the ticket low: You only pay for exactly what you want (ie: if you don't have carry-ons, you can get away with paying less.). This is bullshit. They charge for WATER— tap water— on the plane. It is purely a money making scheme. They don't have repeat customers because they are awful. Oh and the seats are tinier than any flight I've ever been on. Truly the worst flying experience of my life."

Pros: "Went well."

Pros: "Stewardesses were very nice, professional."
Cons: "Spirit seems to be in it more for the money than for providing a service. Really...$50.00 for an item other than a basic carry-on? And then $100.00 if one hadn't checked it earlier. Plus, all the selling that occurred near the gate in my Vegas lay-over...and then the charming but still, a sales pitch...as we approached landing upon my return to Oakland. I will do my best to avoid purchasing tickets from Spirit."

Cons: "Very disappointing.. 1. Lot of hidden charges ($45 for carry on luggage per side) 2. Charges to select seats 3. No complimentary drinks. Even water was for $3 4. They do not accept mobile boarding passes. You need to get a print out of your boarding pass. I mean that is amazing. 5. The most disgusting moment was when i came to know that there was a chewing gum on my tshirt when i removed seat belt. I came to know that it was already there on seat belt. Not sure whose fault it is. Cleaning staff or traveler ? Overall very disappointed with spirit airlines... Will never ever use this airlines again."

Pros: "Nothing"
Cons: "Without notice to us the one and only flight to Chicago left 10 minutes earlier than the time on our tickets. We were standing at the gate over 20 minutes before the flight was to take off but they wouldn't let us board because they lock the doors 20 minutes before the flight takes off. Since they moved the flight time up we were only at the gate about 15 minutes before take off. Several other passengers were in the same position. The entire Frontier staff couldn't have cared less. They tried to say the flight hadn't been moved up but when we showed our tickets they then said it was our fault for not calling in advance to make sure the flight hadn't been moved up! They wouldn't give a refund or credit. We had to pay $300 each to fly on Delta. This company shouldn't be in business."

Pros: "Boarding went smoothly, flight uneventful."
Cons: "No TSA Pre-check! Horrible, but lucky it was a small airport. The seats are really close together and squished if you aren't small. no entertainment on long flight (OAK-ORD). No water."

Pros: "cheap ticket, service was solid, plane clean"
Cons: "bag fees were ridiculous and if I had needed to check bags it would have cost as much as a flight on a better airline."

Pros: "It was a very smooth flying experience"
Cons: "To You should o long waiting. Flight was delayed by 40 mnts. Should provide at least free water"

Pros: "Cheap ticket newer airline and planes fast to board"
Cons: "Plane was cancelled took another day to actually get out"

Cons: "Flight got canceled. There were no contingency plans."

Pros: "Nice people, good landing, good flight in general"
Cons: "I didn't like the repetition at the gate that they would charge $100 for oversized carryons. I think they could avoid this by making it very clear on the computer screens when you buy your ticket"

Pros: "Pilot did a good job - smooth flight from that perspective"
Cons: "The staff was terrible. As we boarded, there were rules and penalties thrown out to make the experience feel more like entering prison vs. what should be a relaxing comfortable flight. On board, the staff continued to put out rules and regulations, and one point brining the book of regulations to a poor woman passenger who had paid for "first class" seats only to find out she couldn't have an infant on her lap. Initial word was she'd have to leave the plane which completely upset her. She said, "Why did you allow me to purchase this ticket if it wasn't allowed to bring my baby?" Later they said it was OK for her to go to a different seat further back for take off and landing. Later, the flight attendant took it upon himself to say that we are welcomed to purchase food on board, but that it is against federal regulations to remove the food and eat it anywhere else. Really?? Even if that is a law, is it really necessary to put all of this negative information out there? I've flown for 30 years and never had this kind of negative experience. The comfort of the seats were terrible. I'm a fit, thin person, and by the end of the flight, my bottom hurt so bad, it took 2 days to feel normal again. I am having to face a flight back to OAK on Spirit and am actually considering purchasing a different ticket to get out of ever stepping on one these planes again! I am telling every one I know NEVER to fly Spirit. This was my first experience and it was the worse flight in my entire life, filled with mean-spirited people and super uncomfortable seats."

Pros: "Everything from checking to landing. It was on time, friendly staff, clean plan.it's amazing. Airlines"

Cons: "The flight was delayed by over 2 hours without an explanation."

Pros: "-took me from point A to point B"
Cons: "-uncomfortable seats with little let room -one member of staff was a little condescending -had to pay $14 extra for a regular seat -carry on prices are ridiculous"

Cons: "seats are cramped"

Pros: "The service was poor. Flight attendant did not even bother to ask me if I wanted to purchase any drinks on the flight. Also flight attendant did not allow me to use to restroom on the aircraft. She shook her finger at me as I walked up and did a turn around sign to indicate that I needed to use the other restroom. I waited 30 minutes to use the other restroom while she stood there in front of the restroom in the front of the aircraft. I have never been restricted to use the restroom before on any airline. The flight also was not full and I asked if I could relocate my seat because the person next to me kept nugging into me and being really close to me and I felt really uncomfortable. Flight attendant told me that the seats are assigned and that they could not do anything about it even though there were plenty of empty seats. They said if I wanted to switch seats then I would have to pay a fee. I have never had an airline tell me that if there were a large amount of empty seats remaining."

Cons: "They charge for the first carryon, they charge to check in at the desk, they charge for all drinks and snacks. In addition there are ads on the carryon compartments and they spend the flight trying to sign you up for their credit card and sell you things. The crew are more like salespeople than service people. The seats don't recline, there's no leg room, even the tray tables seem skimpy because of how tiny they are. Basically the whole is experience feels like being fleeced. Not worth it."

Cons: "Spirit touts being an "ultra low fare" airline, but that is a JOKE! One has to pay for even a carry-on bag, and if you want to sit with your party, you pay again. In addition to my fare for 3 people to fly, we paid another $432 for bags and seat assignments. We paid for no snacks or WATER, which cost $3. I am a bargain hunter, but Spirit was NO bargain! It would have been FAR better (and cheaper) to fly on another carrier. If you don't prinit up your boarding pass, they charge you at the "customer service" desk. My husband joked, "Do we get a seat belt, or is there an extra charge?" That's how it feels, seriously. EVERYTHING that seems like it should be included is not. Be wary!"

Cons: "Their business model is to charge you a lot for everything including carry ons. You need to add at least $50 to make it comparable to even a relatively crummy airline like United"

Read more about Spirit Airlines

Book cheap flights from Oakland to Chicago O'Hare Airport

Recent round-trip flight deals

12/2
Wed
1 stop
Spirit Airlines
7h 46m
OAK - ORD
12/9
Wed
1 stop
Spirit Airlines
15h 14m
ORD - OAK
11/13
Fri
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Multiple Airlines
9h 24m
OAK - ORD
11/16
Mon
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Multiple Airlines
32h 27m
ORD - OAK
11/13
Fri
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Spirit Airlines
9h 24m
OAK - ORD
11/16
Mon
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Spirit Airlines
10h 37m
ORD - OAK
11/19
Thu
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Spirit Airlines
7h 38m
OAK - ORD
11/22
Sun
1 stop
Spirit Airlines
13h 20m
ORD - OAK
11/20
Fri
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Spirit Airlines
7h 38m
OAK - ORD
11/22
Sun
1 stop
Spirit Airlines
13h 20m
ORD - OAK
11/18
Wed
1 stop
Multiple Airlines
15h 28m
OAK - ORD
12/1
Tue
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Multiple Airlines
7h 29m
ORD - OAK
11/26
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Spirit Airlines
7h 38m
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12/15
Tue
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6h 41m
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11/26
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9h 04m
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12/15
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6h 41m
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9h 24m
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13h 41m
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7h 38m
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11/18
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26h 30m
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12h 55m
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10h 58m
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7h 38m
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15h 16m
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13h 41m
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7h 29m
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9h 24m
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Spirit Airlines
9h 10m
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7h 38m
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9h 15m
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25h 10m
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12/3
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10h 31m
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6h 34m
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12/4
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Multiple Airlines
15h 14m
ORD - OAK
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Recent one-way flight deals

11/14
Sat
1 stop
Spirit Airlines
9h 24m
OAK - ORD
11/30
Mon
1 stop
Multiple Airlines
8h 06m
OAK - ORD
11/12
Thu
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Spirit Airlines
9h 24m
OAK - ORD
11/20
Fri
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Spirit Airlines
7h 38m
OAK - ORD
11/13
Fri
1 stop
Spirit Airlines
9h 24m
OAK - ORD
11/5
Thu
2 stops
Spirit Airlines
25h 10m
OAK - ORD
11/23
Mon
1 stop
Multiple Airlines
15h 28m
OAK - ORD
11/26
Thu
1 stop
Spirit Airlines
7h 38m
OAK - ORD
11/11
Wed
2 stops
Spirit Airlines
25h 10m
OAK - ORD
11/18
Wed
2 stops
Multiple Airlines
13h 41m
OAK - ORD
11/21
Sat
2 stops
Multiple Airlines
13h 41m
OAK - ORD
11/9
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Spirit Airlines
9h 24m
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11/7
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9h 24m
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1/7
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Multiple Airlines
24h 56m
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11/5
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9h 24m
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11/13
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Multiple Airlines
14h 50m
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11/20
Fri
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Spirit Airlines
7h 38m
OAK - ORD
11/10
Tue
2 stops
Spirit Airlines
25h 10m
OAK - ORD
12/1
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Spirit Airlines
15h 18m
OAK - ORD
12/16
Wed
1 stop
Spirit Airlines
7h 46m
OAK - ORD
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