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AED 444+ 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 6/5. 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
8 Apr — 15 Apr1
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 3 April 2025.

Cheapest airline

Emirates

Good round-trip deal

AED 652 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 5,046).
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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 3 April 2025.

Wed 7/505:30ORD - PUJ
1 stop8h 15mDelta
Wed 14/514:47PUJ - ORD
1 stop10h 11mDelta
Deal found 2/4AED 1,230
Fri 19/919:45ORD - PUJ
1 stop18h 20mUnited Airlines
Fri 26/915:15PUJ - ORD
1 stop9h 27mUnited Airlines
Deal found 2/4AED 1,528
Wed 28/506:15ORD - PUJ
1 stop8h 18mJetBlue
Sat 7/613:54PUJ - ORD
1 stop9h 26mJetBlue
Deal found 1/4AED 1,656
Sat 7/615:07ORD - PUJ
1 stop10h 06mCopa Airlines
Mon 16/618:36PUJ - ORD
1 stop20h 11mCopa Airlines
Deal found 2/4AED 1,811
Wed 10/901:55ORD - PUJ
1 stop12h 45mAeromexico
Fri 12/917:10PUJ - ORD
1 stop32h 19mAeromexico
Deal found 1/4AED 2,523
Sun 21/919:20ORD - DXB
1 stop17h 05mQatar Airways
Sun 28/905:50DXB - ORD
1 stop18h 15mQatar Airways
Deal found 2/4AED 2,633
Wed 7/519:25ORD - DXB
2 stops18h 35mDelta
Thu 22/501:00DXB - ORD
2 stops27h 20mDelta
Deal found 3/4AED 2,637
Wed 7/518:25MDW - DXB
2 stops19h 10mDelta
Mon 19/500:40DXB - MDW
2 stops23h 40mDelta
Deal found 2/4AED 2,637
Wed 7/519:25ORD - DXB
2 stops18h 35mKLM
Sun 18/500:40DXB - ORD
2 stops22h 30mKLM
Deal found 2/4AED 2,666
Fri 19/911:25ORD - DXB
1 stop15h 55mTurkish Airlines
Fri 26/913:55DXB - ORD
1 stop28h 45mTurkish Airlines
Deal found 1/4AED 2,670
Wed 16/713:40ORD - PUJ
2 stops20h 08mWestJet
Sun 20/715:35PUJ - ORD
2 stops50h 09mWestJet
Deal found 2/4AED 2,784
Wed 17/923:45ORD - AMM
2 stops35h 45mTurkish Airlines
Tue 14/1001:30AMM - ORD
1 stop28h 30mTurkish Airlines
Deal found 3/4AED 2,835

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 3 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

Wed 7/5

05:30-13:22

1 stop6h 52m

Punta Cana

Wed 14/5

13:05-21:20

1 stop9h 15m

AED 1,230

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 19/9

19:45-15:05

1 stop18h 20m

Punta Cana

Fri 26/9

15:15-23:42

1 stop9h 27m

AED 1,528

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 28/5

06:15-15:33

1 stop8h 18m

Punta Cana

Sat 7/6

13:54-22:20

1 stop9h 26m

AED 1,656

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 7/6

15:07-11:05

1 stop18h 58m

Punta Cana

Sat 14/6

05:16-13:47

1 stop9h 31m

AED 1,811

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 10/9

01:55-15:40

1 stop12h 45m

Punta Cana

Mon 15/9

17:10-12:52

1 stop20h 42m

AED 2,523

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Sun 21/9

19:20-20:55

1 stop16h 35m

Dubai Intl

Sun 5/10

05:50-15:05

1 stop18h 15m

AED 2,633

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Wed 7/5

19:25-23:00

2 stops18h 35m

Dubai Intl

Thu 22/5

01:00-19:20

2 stops27h 20m

AED 2,637

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Wed 7/5

18:25-22:35

2 stops19h 10m

Dubai Intl

Mon 19/5

00:40-15:20

2 stops23h 40m

AED 2,637

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Wed 7/5

19:25-23:00

2 stops18h 35m

Dubai Intl

Sun 18/5

00:40-14:10

2 stops22h 30m

AED 2,666

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Fri 19/9

11:25-12:20

1 stop15h 55m

Dubai Intl

Fri 26/9

13:55-09:40

1 stop28h 45m

AED 2,670

Flights are sorted by cheapest return flights first.

Deals found on 2/4

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 28 March 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 3,864). 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.

Emirates

Emirates

From AED 895

Oman Air

Oman Air

From AED 1,284

Etihad Airways

Etihad Airways

From AED 1,039

What are popular destinations to fly to from Chicago?

Some of the most frequent flights departing from Chicago everyday are: New York (1,166 flights per day), Detroit (834 flights per day), and Atlanta (432 flights per day).

Houston Hobby

Houston Hobby

From AED 113

Amman Queen Alia Intl

Amman Queen Alia Intl

From AED 800

Cincinnati Cinci./N. Kentucky

Cincinnati Cinci./N. Kentucky

From AED 145

Kastrup Copenhagen

Kastrup Copenhagen

From AED 502

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

Cincinnati Cinci./N. Kentucky

Cincinnati Cinci./N. Kentucky

From AED 145

Denver Intl

Denver Intl

From AED 176

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
1,287 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.7

Overall

8.1

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.
Singapore Airlines
8.1
Very Good
1,287 reviews
Singapore Airlines
8.1
Very Good
1,287 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.7

Overall

8.1

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.
Emirates
8.0
Very Good
3,193 reviews
Singapore Airlines
8.1
Very Good
1,287 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.7

Overall

8.1

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.
Delta
8.0
Very Good
7,897 reviews
Singapore Airlines
8.1
Very Good
1,287 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.7

Overall

8.1

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.
KLM
7.8
Good
1,323 reviews
Singapore Airlines
8.1
Very Good
1,287 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.7

Overall

8.1

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.
SWISS
7.5
Good
1,574 reviews
Singapore Airlines
8.1
Very Good
1,287 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.7

Overall

8.1

Crew

8.6

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.

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Direct flights from Illinois

Book a direct flight from one of these other cities located in 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 3 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, Athens are the top choices made by travellers year-round.

  • What are the cheapest airlines flying from Chicago to anywhere?

    Looking at our data, Emirates, Etihad Airways, and Royal Jordanian have been found to have the cheapest prices from Chicago. Here are some options available: Emirates flights from Chicago to Dubai Intl (AED 2,908). Etihad Airways flights from Chicago to Abu Dhabi Zayed Intl (AED 2,935). Royal Jordanian flights from Chicago to Amman Queen Alia Intl (AED 2,938).

  • 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 2,475 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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