AED 529+ 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 20/1. 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
28 ene. — 4 feb.1
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 29 diciembre 2025.

Good one-way deal

AED 747 or less
Price to beat on a one-way flight from Chicago Midway.
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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 29 diciembre 2025.

lun. 19/109:32MDW - DXB
2 stops27h 48mDelta
dom. 1/201:30DXB - MDW
2 stops41h 22mDelta
Deal found 27/12AED 2,761
mar. 20/118:14MDW - DXB
2 stops19h 47mKLM
lun. 2/301:55DXB - MDW
2 stops25h 50mKLM
Deal found 29/12AED 2,795
dom. 22/318:34MDW - DXB
2 stops19h 46mDelta
dom. 29/300:40DXB - MDW
2 stops25h 15mDelta
Deal found 29/12AED 2,802
jue. 19/218:20MDW - DXB
2 stops22h 40mMultiple Airlines
mié. 25/201:55DXB - MDW
2 stops25h 50mMultiple Airlines
Deal found 27/12AED 3,125
sáb. 21/318:34MDW - DXB
2 stops19h 46mDelta
lun. 30/301:00DXB - MDW
2 stops25h 54mDelta
Deal found 29/12AED 3,132
mar. 5/513:10MDW - DXB
2 stops24h 50mDelta
sáb. 16/501:00DXB - MDW
2 stops26h 05mDelta
Deal found 27/12AED 3,217
jue. 12/213:29MDW - DXB
2 stops24h 32mDelta
mié. 18/201:30DXB - MDW
2 stops26h 15mDelta
Deal found 29/12AED 3,243
sáb. 14/318:34MDW - DXB
2 stops20h 27mKLM
mié. 18/301:55DXB - MDW
2 stops24h 59mKLM
Deal found 27/12AED 3,452
vie. 6/318:20MDW - DXB
2 stops19h 00mDelta
mié. 11/301:30DXB - MDW
2 stops26h 10mDelta
Deal found 27/12AED 3,529
mié. 22/418:34MDW - DXB
2 stops19h 01mDelta
dom. 3/501:00DXB - MDW
2 stops26h 45mDelta
Deal found 28/12AED 3,606
lun. 19/110:07MDW - DXB
1 stop23h 03mMultiple Airlines
dom. 1/203:05DXB - MDW
1 stop26h 53mMultiple Airlines
Deal found 27/12AED 3,753
jue. 12/212:25MDW - AUH
1 stop21h 05mMultiple Airlines
jue. 19/209:20AUH - MDW
1 stop23h 17mMultiple Airlines
Deal found 28/12AED 3,819

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 29 diciembre 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

lun. 19/1

13:26-23:20

2 stops23h 54m

Dubai Intl

dom. 1/2

01:30-17:55

2 stops26h 25m

AED 2,761

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

mar. 20/1

18:35-23:20

2 stops18h 45m

Dubai Intl

lun. 2/3

01:55-17:45

2 stops25h 50m

AED 2,795

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

jue. 5/2

13:26-00:01

2 stops24h 35m

Dubai Intl

lun. 16/2

01:30-17:45

2 stops26h 15m

AED 2,795

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

mié. 4/3

12:45-23:20

2 stops24h 35m

Dubai Intl

mar. 10/3

01:30-17:54

2 stops25h 24m

AED 2,795

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

dom. 18/1

11:21-00:01

2 stops26h 40m

Dubai Intl

vie. 23/1

06:30-22:22

2 stops25h 52m

AED 2,795

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

mié. 11/3

18:34-00:01

2 stops20h 27m

Dubai Intl

mar. 17/3

01:30-18:40

2 stops26h 10m

AED 2,795

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

mar. 20/1

09:32-23:20

2 stops27h 48m

Dubai Intl

dom. 1/3

01:30-17:37

2 stops26h 07m

AED 2,795

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

mar. 7/4

19:20-23:00

2 stops18h 40m

Dubai Intl

mar. 14/4

01:00-18:45

2 stops26h 45m

AED 2,795

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

mié. 18/2

13:28-00:01

2 stops24h 33m

Dubai Intl

mié. 4/3

06:45-22:31

2 stops25h 46m

AED 2,795

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

sáb. 7/2

13:26-00:01

2 stops24h 35m

Dubai Intl

mié. 18/2

06:45-22:31

2 stops25h 46m

AED 2,795

Flights are sorted by cheapest return flights first.

Deals found on 27/12

Showing 1-10 of 26 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 (166 flights per day), Orlando (144 flights per day), and Detroit (136 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 29 diciembre 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 29 diciembre 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, Orlando Airport, Miami. 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 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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