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AED 386+ 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 8/11. 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
12 Nov — 19 Nov1
1 adult
1 adult, Economy

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 13 October 2025.

Good round-trip deal

AED 545 or less

Good one-way deal

AED 532 or less
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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Find flights from Chicago

Enter your travel dates to find the best prices.

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 13 October 2025.

Tue 2/1209:30ORD - PUJ
Nonstop4h 32mUnited Airlines
Tue 9/1217:20PUJ - ORD
1 stop8h 23mUnited Airlines
Deal found 12/10AED 1,186
Wed 10/1208:45ORD - PUJ
1 stop6h 40mUnited Airlines
Wed 17/1212:56PUJ - ORD
1 stop7h 35mUnited Airlines
Deal found 13/10AED 1,204
Fri 30/109:30ORD - PUJ
Nonstop4h 32mUnited Airlines
Fri 6/214:55PUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 13/10AED 1,216
Fri 14/1108:50ORD - PUJ
1 stop6h 35mUnited Airlines
Fri 21/1114:55PUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 13/10AED 1,223
Wed 14/108:45ORD - PUJ
1 stop6h 40mUnited Airlines
Wed 21/114:55PUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 13/10AED 1,234
Sun 26/1007:52ORD - PUJ
Nonstop4h 30mUnited Airlines
Sun 2/1112:56PUJ - ORD
1 stop12h 47mUnited Airlines
Deal found 12/10AED 1,238
Tue 27/105:50ORD - PUJ
1 stop6h 30mDelta
Thu 5/215:45PUJ - ORD
1 stop10h 09mDelta
Deal found 10/10AED 1,241
Fri 23/105:50ORD - PUJ
1 stop8h 50mDelta
Wed 28/115:45PUJ - ORD
1 stop10h 09mDelta
Deal found 13/10AED 1,256
Mon 15/1208:45ORD - PUJ
1 stop6h 40mUnited Airlines
Mon 22/1215:28PUJ - ORD
1 stop10h 46mUnited Airlines
Deal found 13/10AED 1,260
Tue 28/1008:50ORD - PUJ
1 stop6h 35mUnited Airlines
Thu 30/1013:55PUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 12/10AED 1,267
Fri 23/107:10ORD - PUJ
1 stop7h 30mDelta
Mon 26/118:05PUJ - ORD
1 stop7h 49mDelta
Deal found 13/10AED 1,271
Mon 10/1111:50ORD - DXB
1 stop27h 20mTurkish Airlines
Wed 26/1108:30DXB - ORD
1 stop19h 55mTurkish Airlines
Deal found 11/10AED 2,229

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 13 October 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

Fri 12/12

09:30-16:02

Nonstop4h 32m

Punta Cana

Fri 19/12

16:25-19:38

Nonstop5h 13m

AED 1,204

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 5/12

08:45-17:25

1 stop6h 40m

Punta Cana

Fri 12/12

12:56-21:38

1 stop10h 42m

AED 1,204

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 12/12

08:45-17:25

1 stop6h 40m

Punta Cana

Tue 16/12

17:20-23:43

1 stop8h 23m

AED 1,204

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 10/12

08:45-17:25

1 stop6h 40m

Punta Cana

Wed 17/12

12:56-18:31

1 stop7h 35m

AED 1,204

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 14/11

09:30-16:02

Nonstop4h 32m

Punta Cana

Fri 21/11

14:55-18:08

Nonstop5h 13m

AED 1,204

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 15/12

06:00-17:25

1 stop9h 25m

Punta Cana

Mon 22/12

16:25-19:38

Nonstop5h 13m

AED 1,223

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 25/2

08:45-17:25

1 stop6h 40m

Punta Cana

Wed 4/3

14:55-18:08

Nonstop5h 13m

AED 1,234

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 14/1

08:45-17:25

1 stop6h 40m

Punta Cana

Wed 21/1

14:55-18:08

Nonstop5h 13m

AED 1,234

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 20/1

09:30-16:02

Nonstop4h 32m

Punta Cana

Tue 27/1

12:56-23:39

1 stop12h 43m

AED 1,252

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 29/10

06:00-16:25

1 stop9h 25m

Punta Cana

Sun 2/11

12:56-20:38

1 stop9h 42m

AED 1,252

Flights are sorted by cheapest return flights first.

Deals found on 12/10

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 10 October 2025.

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 75 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, September is the cheapest month in which you can book a flight from Chicago (average of AED 2,152). Flying from Chicago in June will prove the most costly (average of AED 3,239). 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 4,716
Etihad Airways
Etihad Airways
From AED 3,011
Emirates
Emirates
From AED 3,286
Air Canada
Air Canada
From AED 557

What are popular destinations to fly to from Chicago?

Some of the most frequent flights departing from Chicago everyday are: Detroit (1,244 flights per day), New York (1,147 flights per day), and Minneapolis (764 flights per day).

Washington, D.C.
Washington, D.C.
From AED 545
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From AED 3,604
Reykjavik
Reykjavik
From AED 1,570
Cincinnati Cinci./N. Kentucky
Cincinnati Cinci./N. Kentucky
From AED 532

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Cincinnati Cinci./N. Kentucky, with prices starting at AED 532. Explore other affordable destinations below.

Cincinnati Cinci./N. Kentucky
Cincinnati Cinci./N. Kentucky
From AED 532
Washington, D.C.
Washington, D.C.
From AED 545
Dallas/Fort Worth
Dallas/Fort Worth
From AED 545
Denver Intl
Denver Intl
From AED 645

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.
Read reviews from past customers who have flown Emirates from Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Emirates
8.1
Very Good
3,373 reviews
Check prices

Overall

8.1

Crew

8.3

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Food

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

HYD - DXB

Had bad experience this time. Didnt like the seat comforat at all. Additionally, this time Emirates came up with crazy seat arrangement where part of family were placed in different seat and this happened with lot of passengers that day on the flight. I think they did this so that next time we buy seat and pay more. The Indian food was the worst. I booked for Hindu meal well in advance and told at the ticket counter as well but got the regular food. Good bye Emirates, will try Qatar or European airlines next time.
Emirates
8.1
Very Good
3,373 reviews
Emirates
8.1
Very Good
3,373 reviews
Check prices

Overall

8.1

Crew

8.3

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Food

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

HYD - DXB

Had bad experience this time. Didnt like the seat comforat at all. Additionally, this time Emirates came up with crazy seat arrangement where part of family were placed in different seat and this happened with lot of passengers that day on the flight. I think they did this so that next time we buy seat and pay more. The Indian food was the worst. I booked for Hindu meal well in advance and told at the ticket counter as well but got the regular food. Good bye Emirates, will try Qatar or European airlines next time.

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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 13 October 2025.

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

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

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

    Looking at our data, Emirates, Royal Jordanian, and Etihad Airways have been found to have the cheapest prices from Chicago. Here are some options available: Emirates flights from Chicago to Dubai Intl (AED 2,332). Royal Jordanian flights from Chicago to Amman Queen Alia Intl (AED 2,353). Etihad Airways flights from Chicago to Abu Dhabi Zayed Intl (AED 2,935).

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently September; 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 2,196 round trip
    Travel from Chicago to Sharjah from AED 3,059 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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