$1,133+ Cheap flights to Midway

— MDW
18 Nov — 25 Nov1
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

Mon 2/1114:45 -
2 stops21h 02m
Mon 16/1109:30 -
2 stops28h 25m
Deal found 16/10$2,448
Tue 3/1116:05 -
2 stops26h 42m
Wed 18/1106:08 -
3 stops40h 52m
Deal found 17/10$2,920
Mon 16/1120:20 -
3 stops34h 02m
Sun 22/1109:09 -
2 stops25h 41m
Deal found 16/10$3,037

Find flight deals to Midway Airport

Return from

$1,915

One-way from

$1,133

Popular in

October

Cheapest in

March

Average price

$3,523
2/11-16/11
  • 2/11-16/11
  • 6 total stops
  • 69h 18m total
  • Auckland to Chicago
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28/1-31/12
  • 28/1-31/12
  • 3 total stops
  • 39h 08m total
  • Auckland to Chicago
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Highest demand for flights based on searches. 11% potential increase in price ($333 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($92 potential savings vs. average return price).
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Average for return flights in October 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

Thu 28/1

20:20-12:13

2 stops34h 53m

Chicago Midway

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,222

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Wed 28/10

19:00-23:47

2 stops22h 47m

Chicago Midway

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,236

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Wed 2/12

14:45-18:01

2 stops22h 16m

Chicago Midway

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,250

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Tue 5/1

17:30-23:46

3 stops49h 16m

Chicago Midway

Wed 31/12

00:00-18:00

Nonstop0h 00m

$1,708
Fastest return journey

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Tue 24/11

14:45-16:39

2 stops20h 54m

Chicago Midway

Wed 31/12

00:00-18:00

Nonstop0h 00m

$2,056

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Mon 23/11

14:45-16:39

2 stops20h 54m

Chicago Midway

Wed 31/12

00:00-18:00

Nonstop0h 00m

$2,056

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Mon 2/11

14:45-16:47

2 stops21h 02m

Chicago Midway

Mon 16/11

09:30-08:55

2 stops28h 25m

$2,448

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Mon 16/11

20:20-11:22

3 stops34h 02m

Chicago Midway

Sun 22/11

09:09-05:50

2 stops25h 41m

$3,037

AucklandChicago

AKL Auckland Intl - MDW Chicago Midway

AKLMDW

Auckland Intl

Tue 3/11

07:30-23:47

3 stops35h 17m

Chicago Midway

Wed 18/11

06:08-18:00

3 stops40h 52m

$3,090

Flights are sorted by cheapest return flights first.

Deals found on 18/10

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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Deals for Midway flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets to Midway?

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Can Cheapflights find flights to Midway with no change fees?

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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