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AED 496+ Cheap flights from Chicago

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 20/5. 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.
CHI — DXB
5 May — 12 May1
1 adult

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago 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 30 April 2025.

Cheapest airline

Emirates

Good round-trip deal

AED 482 or less

Good one-way deal

AED 215 or less
On average, Emirates currently has the cheapest one-way flight from Chicago (avg. price of AED 5,370).
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Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 30 April 2025.

Sun 11/509:23ORD - PUJ
Nonstop4h 42mUnited Airlines
Thu 15/513:50PUJ - ORD
Nonstop5h 05mUnited Airlines
Deal found 28/4AED 1,065
Tue 12/807:10ORD - PUJ
1 stop6h 22mDelta
Sat 16/815:55PUJ - ORD
1 stop9h 00mDelta
Deal found 27/4AED 1,230
Sat 14/606:15ORD - PUJ
1 stop9h 40mJetBlue
Tue 17/614:55PUJ - ORD
1 stop9h 30mJetBlue
Deal found 28/4AED 1,656
Tue 1/701:07ORD - PUJ
1 stop15h 30mCopa Airlines
Wed 9/705:16PUJ - ORD
1 stop9h 26mCopa Airlines
Deal found 29/4AED 1,811
Fri 15/819:20ORD - DXB
1 stop17h 05mQatar Airways
Sat 30/805:50DXB - ORD
1 stop18h 15mQatar Airways
Deal found 28/4AED 2,762
Tue 2/917:20ORD - DXB
2 stops20h 40mDelta
Mon 8/900:40DXB - ORD
2 stops24h 54mDelta
Deal found 29/4AED 2,769
Tue 2/917:59MDW - DXB
2 stops20h 01mDelta
Mon 8/900:40DXB - MDW
2 stops26h 56mDelta
Deal found 29/4AED 2,769
Sat 13/920:10ORD - AUH
1 stop23h 00mRoyal Jordanian
Sat 27/906:45AUH - ORD
1 stop33h 05mRoyal Jordanian
Deal found 29/4AED 2,780
Wed 3/919:20ORD - DXB
1 stop23h 05mMultiple Airlines
Sat 6/923:25DXB - ORD
1 stop24h 40mMultiple Airlines
Deal found 29/4AED 2,810
Sun 12/1011:25ORD - DXB
1 stop30h 05mTurkish Airlines
Sat 18/1002:00DXB - ORD
1 stop24h 55mTurkish Airlines
Deal found 29/4AED 2,824
Sun 11/516:20ORD - DXB
1 stop21h 40mKLM
Tue 10/601:00DXB - ORD
1 stop22h 10mKLM
Deal found 28/4AED 2,938
Sun 24/820:35ORD - DXB
Nonstop13h 35mEmirates
Fri 5/909:55DXB - ORD
Nonstop14h 50mEmirates
Deal found 29/4AED 3,008

Find flights from Chicago within your budget

Find flights departing from Chicago 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 30 April 2025. In the last 7 days, Cheapflights users made a total of 220,657 searches

Fly to

Dubai

Route

Departure

Return

Price

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 11/5

09:23-15:05

Nonstop4h 42m

Punta Cana

Thu 15/5

13:50-17:55

Nonstop5h 05m

AED 1,065

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 12/8

07:10-14:32

1 stop6h 22m

Punta Cana

Sat 16/8

15:55-23:55

1 stop9h 00m

AED 1,230

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 14/6

06:15-16:55

1 stop9h 40m

Punta Cana

Tue 17/6

14:55-23:25

1 stop9h 30m

AED 1,656

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 1/7

15:07-11:39

1 stop19h 32m

Punta Cana

Sat 5/7

05:16-13:42

1 stop9h 26m

AED 1,811

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Fri 15/8

19:20-21:25

1 stop17h 05m

Dubai Intl

Sat 30/8

05:50-15:05

1 stop18h 15m

AED 2,762

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Tue 2/9

17:20-23:00

2 stops20h 40m

Dubai Intl

Mon 8/9

00:40-16:34

2 stops24h 54m

AED 2,769

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Tue 2/9

17:59-23:00

2 stops20h 01m

Dubai Intl

Mon 8/9

00:40-18:36

2 stops26h 56m

AED 2,769

ChicagoAbu Dhabi

ORD - AUH

ORDAUH

Chicago O'Hare Intl

Sat 13/9

20:10-04:10

1 stop23h 00m

Abu Dhabi Zayed Intl

Sat 27/9

06:45-06:50

1 stop33h 05m

AED 2,780

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Wed 3/9

19:20-03:25

1 stop23h 05m

Dubai Intl

Sat 6/9

23:25-15:05

1 stop24h 40m

AED 2,810

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Sun 12/10

11:25-02:30

1 stop30h 05m

Dubai Intl

Sat 18/10

02:00-17:55

1 stop24h 55m

AED 2,824

Flights are sorted by cheapest return flights first.

Deals found on 28/4

Showing 1-10 of 60 results
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Best time to book a flight from Chicago

Have a flexible travel schedule? Discover the best time to fly from Chicago 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 Chicago

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

When is the best time to book a flight from Chicago?

Use this chart to determine the optimal time to book a return flight from Chicago to Dubai. Price data was last updated on 25 April 2025.

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 57 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago?

Currently, February is the cheapest month in which you can book a flight from Chicago (average of AED 2,178). Flying from Chicago in June will prove the most costly (average of AED 3,507). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Chicago?

For flights departing from Chicago check dates and pricing for the following: Emirates. This airline departs to the following popular destinations: Dubai.

Oman Air

Oman Air

From AED 1,284

Emirates

Emirates

From AED 895

What are popular destinations to fly to from Chicago?

Some of the most frequent flights departing from Chicago everyday are: New York (1,717 flights per day), Detroit (1,278 flights per day), and Los Angeles (719 flights per day).

Houston Hobby

Houston Hobby

From AED 113

Washington, D.C.

Washington, D.C.

From AED 148

Cincinnati Cinci./N. Kentucky

Cincinnati Cinci./N. Kentucky

From AED 145

Abu Dhabi Zayed Intl

Abu Dhabi Zayed Intl

From AED 850

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Minneapolis St Paul, with prices starting at AED 215. Explore other affordable destinations below.

Minneapolis St Paul

Minneapolis St Paul

From AED 58

Houston Hobby

Houston Hobby

From AED 113

Toronto

Toronto

From AED 131

Cincinnati Cinci./N. Kentucky

Cincinnati Cinci./N. Kentucky

From AED 145

Airline reviews for flights from Chicago

Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 220,657 searches.
Singapore Airlines
8.1
Very Good
1,292 reviews
Check prices

Comfort

7.9

Crew

8.6

Overall

8.1

Entertainment

8.0

Boarding

8.2

Food

7.7

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.
Singapore Airlines
8.1
Very Good
1,292 reviews
Singapore Airlines
8.1
Very Good
1,292 reviews
Check prices

Comfort

7.9

Crew

8.6

Overall

8.1

Entertainment

8.0

Boarding

8.2

Food

7.7

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.
Emirates
8.0
Very Good
3,213 reviews
Singapore Airlines
8.1
Very Good
1,292 reviews
Check prices

Comfort

7.9

Crew

8.6

Overall

8.1

Entertainment

8.0

Boarding

8.2

Food

7.7

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.
Delta
8.0
Very Good
7,929 reviews
Singapore Airlines
8.1
Very Good
1,292 reviews
Check prices

Comfort

7.9

Crew

8.6

Overall

8.1

Entertainment

8.0

Boarding

8.2

Food

7.7

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.
KLM
7.8
Good
1,334 reviews
Singapore Airlines
8.1
Very Good
1,292 reviews
Check prices

Comfort

7.9

Crew

8.6

Overall

8.1

Entertainment

8.0

Boarding

8.2

Food

7.7

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.
SWISS
7.5
Good
1,588 reviews
Singapore Airlines
8.1
Very Good
1,292 reviews
Check prices

Comfort

7.9

Crew

8.6

Overall

8.1

Entertainment

8.0

Boarding

8.2

Food

7.7

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

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Direct flights from Illinois

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Related info for your journey

Access useful and relevant information related to your journey from Chicago. 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 30 April 2025.

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

    The most selected flight destinations from Chicago for the current month are Atlanta, Boston, Barcelona-El Prat Airport. While Atlanta, Boston, Mumbai are the top choices made by travellers year-round.

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently February; with June being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • Where are the cheapest places to fly to from Chicago?

    Check out the cheapest flights from Chicago to embark to:
    Travel from Chicago to Dubai from AED 2,182 round trip

  • How does Cheapflights help users find flights from Chicago?

    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 Chicago today with Cheapflights!

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

    It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago.

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

    Certainly. Search results for flights from Chicago 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 Chicago become cheaper?

    Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

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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 Chicago?

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 Chicago today with Cheapflights!

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

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago.

Can Cheapflights find flights from Chicago with no change fees?

Certainly. Search results for flights from Chicago 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 Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

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