AED 577+ 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 22/4. 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 Mar — 23 Mar1
1 adult
1 adult, Economy, 0 bags

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 14 February 2026.

Good one-way deal

AED 747 or less
Price to beat on a one-way flight from Chicago Midway.
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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 14 February 2026.

Wed 4/312:45
MDW
-
DXB
2 stops24h 35m
Delta
Mon 9/301:30
DXB
-
MDW
2 stops25h 24m
Delta
Deal found 13/2AED 2,798
Thu 26/213:49
MDW
-
DXB
2 stops24h 12m
Delta
Wed 4/301:55
DXB
-
MDW
2 stops25h 42m
Delta
Deal found 12/2AED 2,802
Tue 7/413:10
MDW
-
DXB
2 stops24h 50m
Delta
Tue 14/401:00
DXB
-
MDW
2 stops25h 58m
Delta
Deal found 11/2AED 3,037
Thu 26/213:49
MDW
-
DXB
2 stops24h 12m
Delta
Fri 6/301:55
DXB
-
MDW
2 stops30h 36m
Delta
Deal found 11/2AED 3,041
Fri 24/419:16
MDW
-
DXB
2 stops18h 44m
Delta
Mon 27/401:00
DXB
-
MDW
2 stops24h 25m
Delta
Deal found 12/2AED 3,221
Mon 2/312:45
MDW
-
DXB
2 stops24h 35m
Delta
Sun 19/401:00
DXB
-
MDW
2 stops25h 58m
Delta
Deal found 13/2AED 3,224
Wed 29/412:53
MDW
-
DXB
2 stops24h 42m
Delta
Mon 4/500:40
DXB
-
MDW
2 stops26h 56m
Delta
Deal found 11/2AED 3,228
Mon 9/313:10
MDW
-
DXB
2 stops25h 10m
Delta
Wed 11/301:55
DXB
-
MDW
2 stops24h 59m
Delta
Deal found 13/2AED 3,309
Mon 1/613:22
MDW
-
DXB
2 stops24h 38m
Delta
Sun 7/601:00
DXB
-
MDW
2 stops26h 31m
Delta
Deal found 14/2AED 3,434
Fri 27/213:49
MDW
-
DXB
2 stops24h 12m
Delta
Tue 3/301:30
DXB
-
MDW
2 stops26h 07m
Delta
Deal found 13/2AED 3,533
Tue 24/206:10
MDW
-
AUH
1 stop27h 20m
Multiple Airlines
Fri 27/209:20
AUH
-
MDW
1 stop23h 17m
Multiple Airlines
Deal found 10/2AED 4,304
Fri 13/314:41
MDW
-
AUH
1 stop19h 49m
Multiple Airlines
Thu 19/309:20
AUH
-
MDW
1 stop19h 27m
Multiple Airlines
Deal found 13/2AED 4,355

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 14 February 2026. 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

Wed 4/3

10:49-23:20

2 stops26h 31m

Dubai Intl

Tue 10/3

01:30-17:54

2 stops25h 24m

AED 2,798

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Mon 2/3

13:29-00:01

2 stops24h 32m

Dubai Intl

Sun 8/3

01:30-18:40

2 stops26h 10m

AED 2,798

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Sun 10/5

18:36-23:00

2 stops19h 24m

Dubai Intl

Fri 15/5

01:00-18:14

2 stops26h 14m

AED 2,798

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Wed 4/3

13:29-00:01

2 stops24h 32m

Dubai Intl

Sun 8/3

01:30-18:40

2 stops26h 10m

AED 2,798

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Sat 28/2

13:28-00:01

2 stops24h 33m

Dubai Intl

Sun 8/3

01:30-18:40

2 stops26h 10m

AED 2,798

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Tue 17/3

13:10-23:20

2 stops25h 10m

Dubai Intl

Mon 23/3

01:30-17:22

2 stops24h 52m

AED 2,798

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Sun 1/3

18:20-04:30

2 stops24h 10m

Dubai Intl

Sun 8/3

01:30-18:40

2 stops26h 10m

AED 2,798

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Thu 26/2

13:28-00:01

2 stops24h 33m

Dubai Intl

Sun 1/3

01:30-17:45

2 stops26h 15m

AED 2,798

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Sun 1/3

13:28-00:01

2 stops24h 33m

Dubai Intl

Tue 10/3

01:30-17:22

2 stops24h 52m

AED 2,802

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Mon 2/3

18:40-03:00

2 stops22h 20m

Dubai Intl

Fri 6/3

06:30-22:31

2 stops26h 01m

AED 2,802

Flights are sorted by cheapest return flights first.

Deals found on 14/2

Showing 1-10 of 39 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: Atlanta (155 flights per day), Detroit (108 flights per day), and Orlando (74 flights per day).

Washington, D.C.
Washington, D.C.
From AED 545

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

The cheapest city to fly to from Chicago Midway Airport is Washington, D.C., with prices starting at AED 545. Explore other affordable destinations below.

Washington, D.C.
Washington, D.C.
From AED 545

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 14 February 2026.
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 14 February 2026.

  • 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, Phoenix Sky Harbor Intl Airport, Orlando Airport. While Atlanta, Las Vegas, Orlando Airport 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 545 to Washington, D.C. Reagan-National Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for AED 747 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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