Find flights
Airlines

AED 459+ 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 12/5. 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
24 Apr — 1 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 19 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).
Search Deals
Price to beat on a round-trip flight from Chicago.
Search Deals
Price to beat on a one-way flight from Chicago.
Search Deals

Find flights from Chicago

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 19 April 2025.

Tue 13/506:00ORD - PUJ
1 stop8h 35mUnited Airlines
Wed 21/513:50PUJ - ORD
Nonstop5h 05mUnited Airlines
Deal found 19/4AED 1,263
Tue 20/507:05ORD - PUJ
1 stop6h 40mDelta
Wed 28/513:05PUJ - ORD
1 stop9h 15mDelta
Deal found 17/4AED 1,535
Sun 1/615:07ORD - PUJ
1 stop18h 42mCopa Airlines
Sun 8/618:36PUJ - ORD
1 stop20h 11mCopa Airlines
Deal found 18/4AED 1,583
Fri 10/1006:00ORD - PUJ
1 stop10h 14mJetBlue
Tue 14/1011:30PUJ - ORD
1 stop10h 24mJetBlue
Deal found 18/4AED 1,778
Sat 30/817:25ORD - PUJ
2 stops18h 30mSouthwest
Sat 6/914:40PUJ - ORD
1 stop7h 50mSouthwest
Deal found 17/4AED 2,149
Fri 22/819:20ORD - DXB
1 stop29h 55mQatar Airways
Mon 1/905:50DXB - ORD
1 stop18h 15mQatar Airways
Deal found 18/4AED 2,659
Sat 13/923:45ORD - DXB
1 stop27h 35mTurkish Airlines
Sun 5/1002:00DXB - ORD
1 stop29h 00mTurkish Airlines
Deal found 19/4AED 2,663
Tue 7/1011:19ORD - DXB
2 stops26h 16mDelta
Mon 13/1001:00DXB - ORD
2 stops41h 00mDelta
Deal found 18/4AED 2,667
Tue 23/920:10ORD - AUH
1 stop23h 00mRoyal Jordanian
Sat 27/906:45AUH - ORD
1 stop33h 05mRoyal Jordanian
Deal found 19/4AED 2,780
Sat 23/814:00MDW - DXB
2 stops24h 00mDelta
Wed 3/900:40DXB - MDW
2 stops26h 23mDelta
Deal found 18/4AED 2,813
Thu 1/514:10ORD - DXB
2 stops29h 25mMultiple Airlines
Sun 4/523:00DXB - ORD
2 stops27h 34mMultiple Airlines
Deal found 17/4AED 2,869
Wed 10/911:25ORD - AMM
1 stop33h 25mTurkish Airlines
Wed 24/918:50AMM - ORD
2 stops22h 50mTurkish Airlines
Deal found 18/4AED 2,876

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 19 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

Tue 13/5

06:00-15:35

1 stop8h 35m

Punta Cana

Wed 21/5

13:50-17:55

Nonstop5h 05m

AED 1,263

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 20/5

07:05-14:45

1 stop6h 40m

Punta Cana

Wed 28/5

13:05-21:20

1 stop9h 15m

AED 1,535

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 1/6

15:07-10:49

1 stop18h 42m

Punta Cana

Sun 8/6

18:36-13:47

1 stop20h 11m

AED 1,583

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 10/10

06:00-17:14

1 stop10h 14m

Punta Cana

Tue 14/10

11:30-20:54

1 stop10h 24m

AED 1,778

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 30/8

17:25-12:55

2 stops18h 30m

Punta Cana

Sat 6/9

14:40-21:30

1 stop7h 50m

AED 2,149

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Fri 22/8

19:20-10:15

1 stop29h 55m

Dubai Intl

Mon 1/9

05:50-15:05

1 stop18h 15m

AED 2,659

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Sat 13/9

23:45-05:55

1 stop21h 10m

Dubai Intl

Mon 6/10

07:35-22:00

1 stop23h 25m

AED 2,663

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Tue 7/10

11:19-22:35

2 stops26h 16m

Dubai Intl

Mon 13/10

01:00-09:00

2 stops41h 00m

AED 2,667

ChicagoAbu Dhabi

ORD - AUH

ORDAUH

Chicago O'Hare Intl

Tue 23/9

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

MDW - DXB

MDWDXB

Chicago Midway

Sat 23/8

14:00-23:00

2 stops24h 00m

Dubai Intl

Wed 3/9

00:40-18:03

2 stops26h 23m

AED 2,813

Flights are sorted by cheapest return flights first.

Deals found on 19/4

Showing 1-10 of 60 results
1
2
3
...
6

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 18 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 3,632). 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 (1,678 flights per day), Detroit (1,164 flights per day), and Los Angeles (663 flights per day).

Washington, D.C.

Washington, D.C.

From AED 108

Houston Hobby

Houston Hobby

From AED 113

Amman Queen Alia Intl

Amman Queen Alia Intl

From AED 800

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

Washington, D.C.

Washington, D.C.

From AED 108

Houston Hobby

Houston Hobby

From AED 113

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
1,291 reviews
Check prices

Overall

8.1

Crew

8.6

Entertainment

8.0

Comfort

7.9

Food

7.7

Boarding

8.2

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
1,291 reviews
Singapore Airlines
8.1
Very Good
1,291 reviews
Check prices

Overall

8.1

Crew

8.6

Entertainment

8.0

Comfort

7.9

Food

7.7

Boarding

8.2

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
3,201 reviews
Singapore Airlines
8.1
Very Good
1,291 reviews
Check prices

Overall

8.1

Crew

8.6

Entertainment

8.0

Comfort

7.9

Food

7.7

Boarding

8.2

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
7,920 reviews
Singapore Airlines
8.1
Very Good
1,291 reviews
Check prices

Overall

8.1

Crew

8.6

Entertainment

8.0

Comfort

7.9

Food

7.7

Boarding

8.2

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
1,331 reviews
Singapore Airlines
8.1
Very Good
1,291 reviews
Check prices

Overall

8.1

Crew

8.6

Entertainment

8.0

Comfort

7.9

Food

7.7

Boarding

8.2

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
1,582 reviews
Singapore Airlines
8.1
Very Good
1,291 reviews
Check prices

Overall

8.1

Crew

8.6

Entertainment

8.0

Comfort

7.9

Food

7.7

Boarding

8.2

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.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Direct flights from Illinois

Book a direct flight from one of these other cities located in Illinois.
Direct flights from St. Louis

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 19 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 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 2,939).

  • 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 2,343 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!

See more FAQs

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!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights