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AED 360+ 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 22/1. 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.
CHI — DXB
9 Jan — 16 Jan1
1 adult
1 adult, Economy, 0 bags

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 10 December 2025.

Good round-trip deal

AED 652 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

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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 10 December 2025.

Sun 4/109:15ORD - PUJ
Nonstop4h 32mUnited Airlines
Wed 14/116:25PUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 7/12AED 966
Sun 11/108:52ORD - PUJ
1 stop6h 33mUnited Airlines
Thu 15/117:20PUJ - ORD
1 stop8h 19mUnited Airlines
Deal found 7/12AED 1,021
Mon 2/306:00ORD - PUJ
1 stop9h 25mUnited Airlines
Mon 9/313:55PUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 7/12AED 1,076
Mon 19/109:30ORD - PUJ
Nonstop4h 32mUnited Airlines
Mon 26/117:20PUJ - ORD
1 stop8h 19mUnited Airlines
Deal found 7/12AED 1,094
Tue 7/405:45ORD - PUJ
1 stop8h 45mUnited Airlines
Tue 14/415:35PUJ - ORD
1 stop9h 09mUnited Airlines
Deal found 7/12AED 1,109
Thu 8/108:52ORD - PUJ
1 stop6h 33mUnited Airlines
Thu 15/112:56PUJ - ORD
1 stop12h 43mUnited Airlines
Deal found 7/12AED 1,113
Sat 11/411:27ORD - PUJ
Nonstop4h 45mArajet
Sun 19/418:00PUJ - ORD
Nonstop5h 10mArajet
Deal found 8/12AED 1,157
Tue 14/405:45ORD - PUJ
1 stop8h 45mUnited Airlines
Tue 21/415:35PUJ - ORD
1 stop9h 09mUnited Airlines
Deal found 7/12AED 1,182
Mon 9/307:52ORD - PUJ
Nonstop4h 30mUnited Airlines
Mon 16/315:25PUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 7/12AED 1,186
Sat 10/108:52ORD - PUJ
1 stop6h 33mUnited Airlines
Sat 17/112:56PUJ - ORD
1 stop7h 41mUnited Airlines
Deal found 7/12AED 1,205
Wed 11/307:52ORD - PUJ
Nonstop4h 30mUnited Airlines
Wed 18/311:56PUJ - ORD
1 stop7h 55mUnited Airlines
Deal found 7/12AED 1,234
Fri 13/321:20ORD - DXB
1 stop18h 50mTurkish Airlines
Sun 22/309:30DXB - ORD
1 stop18h 55mTurkish Airlines
Deal found 9/12AED 2,468

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 10 December 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 4/1

08:51-17:25

1 stop6h 34m

Punta Cana

Wed 14/1

16:25-19:38

Nonstop5h 13m

AED 1,069

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 16/1

14:13-02:05

1 stop9h 52m

Punta Cana

Tue 20/1

14:49-00:24

1 stop11h 35m

AED 1,300

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 4/2

14:22-11:35

1 stop19h 13m

Punta Cana

Wed 11/2

05:43-00:04

1 stop20h 21m

AED 1,300

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 20/1

05:30-14:20

1 stop6h 50m

Punta Cana

Fri 23/1

16:55-23:55

1 stop9h 00m

AED 1,344

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 3/3

07:00-16:21

1 stop7h 21m

Punta Cana

Wed 4/3

17:46-07:58

1 stop16h 12m

AED 1,344

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 7/4

05:45-15:30

1 stop8h 45m

Punta Cana

Tue 14/4

14:20-00:30

1 stop11h 10m

AED 1,344

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 4/3

07:00-16:21

1 stop7h 21m

Punta Cana

Tue 10/3

17:05-10:05

1 stop18h 00m

AED 1,344

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 13/1

07:00-16:21

1 stop7h 21m

Punta Cana

Fri 23/1

18:06-23:55

1 stop7h 49m

AED 1,344

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 22/4

08:06-17:31

1 stop8h 25m

Punta Cana

Sun 26/4

05:35-13:58

1 stop9h 23m

AED 1,355

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 12/1

18:15-16:21

2 stops20h 06m

Punta Cana

Fri 23/1

18:06-09:41

2 stops17h 35m

AED 1,359

Flights are sorted by cheapest return flights first.

Deals found on 8/12

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 5 December 2025.

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 49 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, November is the cheapest month in which you can book a flight from Chicago (average of AED 2,060). 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.

Etihad Airways
Etihad Airways
From AED 3,011
Air Canada
Air Canada
From AED 557
Emirates
Emirates
From AED 3,286

What are popular destinations to fly to from Chicago?

Some of the most frequent flights departing from Chicago everyday are: New York (1,490 flights per day), Detroit (948 flights per day), and Minneapolis (655 flights per day).

Washington, D.C.
Washington, D.C.
From AED 545
Dubai Intl
Dubai Intl
From AED 2,295
Zurich
Zurich
From AED 3,396
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From AED 3,654

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
Denver Intl
Denver Intl
From AED 645
Orlando
Orlando
From AED 789

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 and United Airlines 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
3,433 reviews
Check prices

Boarding

8.1

Entertainment

8.2

Comfort

8.0

Crew

8.3

Food

7.9

Overall

8.1

Reviews

1 / 20
10.0
Excellent

Peter,Nov 2025

HKT - DXB

Great flight and the best food I’ve had on a plane
Emirates
8.1
Very Good
3,433 reviews
Emirates
8.1
Very Good
3,433 reviews
Check prices

Boarding

8.1

Entertainment

8.2

Comfort

8.0

Crew

8.3

Food

7.9

Overall

8.1

Reviews

1 / 20
10.0
Excellent

Peter,Nov 2025

HKT - DXB

Great flight and the best food I’ve had on a plane
United Airlines
7.4
Good
9,092 reviews
Emirates
8.1
Very Good
3,433 reviews
Check prices

Boarding

8.1

Entertainment

8.2

Comfort

8.0

Crew

8.3

Food

7.9

Overall

8.1

Reviews

1 / 20
10.0
Excellent

Peter,Nov 2025

HKT - DXB

Great flight and the best food I’ve had on a plane

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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 10 December 2025.

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

    The most selected flight destinations from Chicago for the current month are Ahmedabad, Mumbai, Atlanta. 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, Etihad Airways, United Airlines, and Emirates have been found to have the cheapest prices from Chicago. Here are some options available: Etihad Airways flights from Chicago to Abu Dhabi Zayed Intl (AED 2,935). United Airlines flights from Chicago to Dubai Intl (AED 3,029). Emirates flights from Chicago to Dubai Intl (AED 3,281).

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently November; 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 2,163 round trip
    Travel from Chicago to Sharjah from AED 2,706 round trip
    Travel from Chicago to Dubai from AED 3,614 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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