Find cheap flights to Chicago

• Looking for cheap airfare to Chicago? 25% of our users found tickets to Chicago for the following prices or less: From Auckland Intl $1,161 one-way - $1,767 round-trip
• Book at least 1 week before departure in order to get a below-average price.
• High season is considered to be June, July and August. The cheapest month to fly from New Zealand is November.
• Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

• What is the cheapest flight to Chicago?

  If travelling to Chicago, the cheapest city to fly from in the last 3 days was Auckland, with flights as low as $1,657 one-way and $3,060 return. Flights from Auckland are the most searched and start at $198 for a return trip.

• How far is Chicago from central Chicago?

  The distance between Chicago and the city centre of Chicago is 26 km.

• How much is a flight to Chicago?

  On average, a flight to Chicago costs $3,159. The cheapest price found on KAYAK in the last 2 weeks cost $889 and departed from Auckland Intl Airport.

• What is the cheapest month to fly to Chicago?

  The cheapest month for flights to Chicago is November. On the other hand, the most expensive months are June and July.

• Which airlines have a flexible cancellation policy for flights to Chicago due to COVID-19?

  Air New Zealand and United Airlines have waived their change and cancellation fees on flights to Chicago. Confirm policies on booking site.

• How does KAYAK find such low prices on flights to Chicago?

  KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

• How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

  KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

• What is the Hacker Fare option on flights to Chicago?

  Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back with another airline.

• What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

  Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Book Cheap Chicago Plane Tickets

Recent return flight deals

28/11Tue

2 stopsUnited Airlines

46h 22mCHC-ORD

14/12Thu

2 stopsUnited Airlines

43h 05mORD-CHC

$1,847

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28/11Tue

2 stopsUnited Airlines

55h 03mCHC-ORD

14/12Thu

1 stopUnited Airlines

42h 14mORD-CHC

$1,919

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1/8Tue

2 stopsMultiple Airlines

24h 10mAKL-ORD

18/8Fri

2 stopsMultiple Airlines

25h 28mORD-AKL

$1,933

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6/8Sun

directUnited Airlines

15h 05mAKL-ORD

14/8Mon

2 stopsUnited Airlines

24h 12mORD-AKL

$1,985

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3/8Thu

2 stopsQantas Airways

29h 52mAKL-ORD

17/8Thu

2 stopsQantas Airways

38h 20mORD-AKL

$1,995

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1/8Tue

2 stopsMultiple Airlines

24h 10mAKL-ORD

15/8Tue

2 stopsMultiple Airlines

25h 57mORD-AKL

$2,003

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31/7Mon

2 stopsAmerican Airlines

24h 57mAKL-ORD

16/8Wed

2 stopsAmerican Airlines

25h 55mORD-AKL

$2,013

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6/8Sun

directUnited Airlines

15h 05mAKL-ORD

18/8Fri

1 stopUnited Airlines

23h 04mORD-AKL

$2,015

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1/8Tue

2 stopsMultiple Airlines

24h 10mAKL-ORD

20/8Sun

2 stopsMultiple Airlines

25h 28mORD-AKL

$2,038

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3/8Thu

2 stopsAmerican Airlines

27h 10mAKL-ORD

18/8Fri

2 stopsAmerican Airlines

25h 55mORD-AKL

$2,043

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3/8Thu

1 stopAir New Zealand

24h 38mAKL-ORD

17/8Thu

1 stopAir New Zealand

19h 28mORD-AKL

$2,059

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4/8Fri

2 stopsAmerican Airlines

24h 34mAKL-ORD

15/8Tue

1 stopAmerican Airlines

41h 00mORD-AKL

$2,068

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3/8Thu

2 stopsAmerican Airlines

27h 10mAKL-ORD

14/8Mon

2 stopsAmerican Airlines

26h 07mORD-AKL

$2,073

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19/7Wed

1 stopUnited Airlines

26h 49mAKL-ORD

18/8Fri

directUnited Airlines

16h 25mORD-AKL

$2,093

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3/8Thu

2 stopsAmerican Airlines

27h 10mAKL-ORD

19/8Sat

2 stopsAmerican Airlines

25h 55mORD-AKL

$2,102

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22/11Wed

1 stopQantas Airways

28h 37mAKL-ORD

18/12Mon

1 stopQantas Airways

21h 20mORD-AKL

$2,119

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28/11Tue

1 stopAir New Zealand

38h 50mCHC-ORD

14/12Thu

1 stopAir New Zealand

42h 14mORD-CHC

$2,132

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31/7Mon

2 stopsQantas Airways

26h 27mAKL-ORD

15/8Tue

2 stopsQantas Airways

26h 35mORD-AKL

$2,182

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31/7Mon

2 stopsQantas Airways

26h 27mAKL-ORD

19/8Sat

2 stopsQantas Airways

26h 35mORD-AKL

$2,187

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6/8Sun

2 stopsQantas Airways

27h 16mAKL-ORD

16/8Wed

2 stopsQantas Airways

26h 35mORD-AKL

$2,271

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$1,980 or less$2,010 or less$2,070 or less$2,120 or less$2,270 or less

Recent one-way flight deals

25/7Tue

2 stopsMultiple Airlines

31h 01mAKL-ORD

$946

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14/11Tue

2 stopsQantas Airways

25h 20mAKL-ORD

$971

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22/11Wed

directAir New Zealand

14h 45mAKL-ORD

$974

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12/6Mon

1 stopUnited Airlines

28h 10mAKL-ORD

$984

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6/6Tue

1 stopMultiple Airlines

39h 15mWLG-ORD

$984

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6/6Tue

2 stopsMultiple Airlines

33h 25mWLG-ORD

$989

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18/7Tue

2 stopsMultiple Airlines

24h 10mAKL-ORD

$989

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16/11Thu

2 stopsQantas Airways

25h 20mAKL-ORD

$996

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19/11Sun

1 stopAir Canada

20h 51mAKL-ORD

$997

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11/11Sat

2 stopsQantas Airways

25h 20mAKL-ORD

$1,001

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20/11Mon

1 stopAmerican Airlines

24h 36mAKL-ORD

$1,002

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19/11Sun

directAir New Zealand

14h 45mAKL-ORD

$1,004

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12/11Sun

1 stopAir Canada

25h 00mAKL-ORD

$1,006

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18/11Sat

2 stopsDelta

25h 07mAKL-ORD

$1,016

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25/7Tue

1 stopUnited Airlines

30h 38mAKL-ORD

$1,021

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11/11Sat

1 stopQantas Airways

26h 31mAKL-ORD

$1,026

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12/6Mon

2 stopsUnited Airlines

27h 48mAKL-ORD

$1,034

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20/7Thu

1 stopAir New Zealand

21h 50mAKL-ORD

$1,067

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18/7Tue

1 stopAir New Zealand

20h 12mAKL-ORD

$1,074

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18/7Tue

2 stopsUnited Airlines

33h 59mAKL-ORD

$1,077

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Qantas AirwaysAir New ZealandUnited AirlinesAir CanadaAmerican AirlinesDelta

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$980 or less$1,000 or less$1,030 or less$1,080 or less

Recent domestic flight deals

13/9Wed

directDelta

2h 46mBOS-ORD

19/9Tue

directDelta

2h 23mORD-BOS

$162

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20/6Tue

directSpirit Airlines

2h 32mDFW-ORD

26/6Mon

directSpirit Airlines

2h 28mORD-DFW

$169

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20/6Tue

1 stopSpirit Airlines

7h 05mDFW-ORD

26/6Mon

directSpirit Airlines

2h 28mORD-DFW

$174

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2/9Sat

directUnited Airlines

2h 38mEWR-ORD

9/9Sat

directUnited Airlines

2h 10mORD-EWR

$176

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15/8Tue

directDelta

2h 37mLGA-ORD

22/8Tue

directDelta

2h 14mORD-LGA

$176

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Direct1 stop2+ stops

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$160 or less$170 or less$180 or less