$953+ Cheap flights to Midway

— MDW
9 Oct — 16 Oct1
1 adult
1 adult, Economy, 0 bags

Flights to Midway in 2026

Enter your travel dates to find the best prices.

Cheapest flights to Midway Airport

Thu 5/1114:45 -
2 stops26h 48m
Sun 15/1113:31 -
2 stops24h 24m
Deal found 7/9$4,811

Find flight deals to Midway Airport

Return from

$2,132

One-way from

$953

Popular in

May

Cheapest in

November

Average price

$2,628
Cathay Pacific
  • Cathay Pacific
  • 5/11-15/11
  • 2 total stops
  • 68h 50m total
  • Auckland to Chicago
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23/10-31/12
  • 23/10-31/12
  • 3 total stops
  • 50h 43m total
  • Auckland to Chicago
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Highest demand for flights based on searches. 8% potential increase in price ($216 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease ($52 potential savings vs. average return price).
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Average for return flights in September 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Route

Departure

Return

Price

Cheapest return flight

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Fri 23/10

15:00-23:43

3 stops50h 43m

Chicago Midway

Wed 31/12

00:00-18:00

Nonstop0h 00m

$953
Fastest return journey

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Thu 29/10

07:30-23:47

3 stops34h 17m

Chicago Midway

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,210

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Sat 9/1

17:10-16:47

3 stops42h 37m

Chicago Midway

Wed 31/12

00:00-18:00

Nonstop0h 00m

$2,341

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Fri 8/1

20:20-14:48

3 stops37h 28m

Chicago Midway

Wed 31/12

00:00-18:00

Nonstop0h 00m

$2,848

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Thu 5/11

14:45-22:33

2 stops26h 48m

Chicago Midway

Sun 15/11

13:31-08:55

2 stops24h 24m

$4,811

Flights are sorted by cheapest return flights first.

Deals found on 8/9

Sorted by cheapest first

Best time to book a flight to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway with our price prediction graph.
Estimated return price

Cheapflights Insights

Everything you need to know about your flight to Chicago Midway Airport

Rainfall in Midway by month

In terms of precipitation, rainfall in Midway ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Midway when rainfall is around 43.0 mm.

Temperature in Midway by month

If weather is an important factor for your trip to Midway, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

FAQs about flying to Midway

  • Can I find cheaper flights to Midway if I am willing to have stopovers?

    Yes, flights with stopovers are often cheaper than direct flights. Keep an eye out for flight deals to Midway on Cheapflights that require 1 or 2 stops for potential cost savings.

  • Does Chicago Midway have rental cars?

    Yes. Those touching down at Chicago Midway can take advantage of the car hire services offered upon their arrival.

  • Are there hotels close to Chicago Midway?

    Yes. Chicago Midway has hotels nearby for those requiring accommodations. Midway Airport 2 Bedroom With Full Kitchen is the closest property to Chicago Midway (0.0 km away from Chicago Midway).

Browse thousands of different options on Cheapflights for your next trip

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Users can book flights with no change fees policies with our dedicated filters. Book flights to Midway flexibly with Cheapflights today.

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