AED 481+ Cheap flights from Chicago Midway Airport

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 26/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — DXB
16 Nov — 23 Nov1
1 adult
1 adult, Economy

What to know about flights from Midway

Discover essential information about flights departing from Midway, including flight schedules, destinations, airlines operating at the Midway airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 17 October 2025.

Good round-trip deal

AED 652 or less

Good one-way deal

AED 532 or less
Price to beat on a round-trip flight from Chicago Midway.
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Price to beat on a one-way flight from Chicago Midway.
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Find flights from Midway

Enter your travel dates to find the best prices.

Cheapest flights from Midway
Explore the most affordable flight options available from Midway. Find the lowest fares based on data from user searches, with prices last updated on 17 October 2025.

Mon 17/1117:34MDW - DXB
2 stops20h 27mKLM
Wed 19/1101:55DXB - MDW
2 stops24h 43mKLM
Deal found 16/10AED 2,677
Mon 3/1113:08MDW - DXB
2 stops24h 53mDelta
Tue 11/1101:55DXB - MDW
2 stops26h 13mDelta
Deal found 14/10AED 2,681
Sun 30/1113:15MDW - DXB
2 stops24h 05mDelta
Fri 5/1201:55DXB - MDW
2 stops26h 11mDelta
Deal found 16/10AED 2,714
Sat 29/1113:15MDW - DXB
2 stops24h 46mDelta
Sat 6/1211:20DXB - MDW
2 stops38h 58mDelta
Deal found 15/10AED 2,718
Mon 27/1018:23MDW - DXB
2 stops20h 38mDelta
Sun 9/1101:30DXB - MDW
2 stops41h 24mDelta
Deal found 16/10AED 2,732
Tue 9/1213:14MDW - DXB
2 stops24h 06mDelta
Mon 15/1201:30DXB - MDW
2 stops25h 13mDelta
Deal found 16/10AED 2,751
Sun 7/1213:14MDW - DXB
2 stops24h 06mMultiple Airlines
Tue 16/1201:30DXB - MDW
2 stops26h 30mMultiple Airlines
Deal found 15/10AED 2,776
Wed 5/1113:08MDW - DXB
2 stops24h 53mDelta
Tue 18/1101:30DXB - MDW
2 stops26h 48mDelta
Deal found 16/10AED 2,861
Sun 1/314:00MDW - DXB
2 stops24h 01mKLM
Sat 7/301:55DXB - MDW
2 stops25h 39mKLM
Deal found 15/10AED 3,096
Wed 26/1113:15MDW - DXB
2 stops24h 46mDelta
Mon 1/1201:55DXB - MDW
2 stops26h 05mDelta
Deal found 17/10AED 3,133
Sat 8/1111:10MDW - DXB
2 stops26h 51mDelta
Sat 15/1101:55DXB - MDW
2 stops26h 13mDelta
Deal found 16/10AED 3,191
Fri 31/1018:35MDW - DXB
2 stops20h 26mDelta
Sat 15/1101:55DXB - MDW
2 stops26h 13mDelta
Deal found 15/10AED 3,279

Find flights from Midway within your budget

 
Find flights departing from Midway that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 17 October 2025. In the last 7 days, Cheapflights users made a total of 220,657 searches

Fly to

Dubai

Route

Departure

Return

Price

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Mon 2/2

17:25-00:01

2 stops20h 36m

Dubai Intl

Wed 4/2

01:55-16:25

2 stops24h 30m

AED 2,677

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Mon 10/11

13:15-00:01

2 stops24h 46m

Dubai Intl

Tue 25/11

01:55-16:39

2 stops24h 44m

AED 2,677

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Thu 13/11

13:47-23:20

2 stops23h 33m

Dubai Intl

Wed 19/11

01:30-16:38

2 stops25h 08m

AED 2,677

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Mon 17/11

17:34-00:01

2 stops20h 27m

Dubai Intl

Wed 19/11

01:55-16:38

2 stops24h 43m

AED 2,677

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Fri 27/2

14:00-00:01

2 stops24h 01m

Dubai Intl

Fri 6/3

01:30-18:08

2 stops26h 38m

AED 2,677

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Mon 9/3

06:00-23:20

2 stops32h 20m

Dubai Intl

Wed 11/3

01:55-09:56

2 stops41h 01m

AED 2,677

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Mon 17/11

17:34-00:01

2 stops20h 27m

Dubai Intl

Tue 9/12

01:30-18:00

2 stops26h 30m

AED 2,677

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Mon 23/2

09:30-23:20

2 stops27h 50m

Dubai Intl

Sat 28/2

01:55-18:34

2 stops26h 39m

AED 2,677

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Fri 9/1

13:00-00:01

2 stops25h 01m

Dubai Intl

Fri 16/1

01:55-16:25

2 stops24h 30m

AED 2,677

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Sat 10/1

13:00-00:01

2 stops25h 01m

Dubai Intl

Sat 17/1

01:55-21:46

2 stops29h 51m

AED 2,677

Flights are sorted by cheapest return flights first.

Deals found on 16/10

Showing 1-10 of 28 results
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Best time to book a flight from Midway

Have a flexible travel schedule? Discover the best time to fly from Midway with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Midway

Get recent, data-driven insights about flights from Midway including ideal travel times, pricing trends, and more.

What are popular destinations to fly to from Chicago Midway Airport?

Some of the most frequent flights departing from Chicago Midway Airport everyday are: Detroit (210 flights per day), Atlanta (157 flights per day), and Orlando (114 flights per day).

Washington, D.C.
Washington, D.C.
From AED 545
Cincinnati Cinci./N. Kentucky
Cincinnati Cinci./N. Kentucky
From AED 532
Denver Intl
Denver Intl
From AED 645

What is the cheapest place to fly to from Chicago Midway Airport?

The cheapest city to fly to from Chicago Midway Airport is Cincinnati Cinci./N. Kentucky, with prices starting at AED 532. Explore other affordable destinations below.

Cincinnati Cinci./N. Kentucky
Cincinnati Cinci./N. Kentucky
From AED 532
Washington, D.C.
Washington, D.C.
From AED 545
Denver Intl
Denver Intl
From AED 645

Browse thousands of different options on Cheapflights for your next trip

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Alternate flight departure points to Midway

Consider leaving from one of these other departure points that are located a short distance from Midway. Flight origins were last updated on 17 October 2025.
Flights from St. Louis
Flights from O'Hare Intl
Flights from Belleville
Flights from Springfield

Related info for your journey

Access useful and relevant information related to your journey from Midway. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 17 October 2025.

  • What are the most popular destinations to fly to from Chicago Midway Airport?

    The most selected flight destinations from Chicago Midway Airport for the current month are Atlanta, Las Vegas, Orlando Airport. While Atlanta, Las Vegas, Cancún are the top choices made by travellers year-round.

  • What is the cheapest flight from Chicago Midway Airport to anywhere?

    Users have flown out of Chicago Midway Airport for as low as AED 532 to Cincinnati (prices may vary depending on the airline and departure time). On average, users have booked flights for AED 644 to fly from Chicago Midway Airport.

  • How does Cheapflights help users find flights from Midway?

    900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Midway today with Cheapflights!

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

    By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Midway.

  • Can Cheapflights find flights from Midway with no change fees?

    Certainly. Search results for flights from Midway shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

  • Can Cheapflights notify me if prices for flights from Midway become cheaper?

    Yes! Start tracking prices for flights from Midway today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Midway?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Midway today with Cheapflights!

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

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Midway.

Can Cheapflights find flights from Midway with no change fees?

Certainly. Search results for flights from Midway shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Midway become cheaper?

Yes! Start tracking prices for flights from Midway today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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