Find flights
Airlines

AED 323+ 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 25/1. 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 Feb — 16 Feb1
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 January 2026.

Good round-trip deal

AED 1,087 or less

Good one-way deal

AED 747 or less
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

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 10 January 2026.

Tue 24/207:00ORD - PUJ
1 stop7h 36mSpirit Airlines
Mon 2/317:47PUJ - ORD
1 stop8h 00mSpirit Airlines
Deal found 7/1AED 1,010
Fri 6/205:15ORD - PUJ
1 stop9h 21mSpirit Airlines
Tue 10/217:47PUJ - ORD
1 stop8h 00mSpirit Airlines
Deal found 7/1AED 1,065
Thu 26/205:15ORD - PUJ
1 stop9h 21mSpirit Airlines
Mon 2/317:47PUJ - ORD
1 stop8h 00mSpirit Airlines
Deal found 8/1AED 1,116
Sat 7/210:27ORD - PUJ
Nonstop4h 45mWorldTicket
Tue 10/219:30PUJ - ORD
Nonstop5h 10mWorldTicket
Deal found 8/1AED 1,278
Sun 8/205:15ORD - PUJ
1 stop9h 21mSpirit Airlines
Sun 15/217:47PUJ - ORD
1 stop8h 00mSpirit Airlines
Deal found 9/1AED 1,344
Thu 26/306:44ORD - PUJ
1 stop7h 41mJetBlue
Wed 1/412:05PUJ - ORD
1 stop10h 28mJetBlue
Deal found 10/1AED 1,388
Tue 3/208:45ORD - PUJ
Nonstop4h 32mUnited Airlines
Wed 4/216:25PUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 8/1AED 1,425
Mon 16/306:00ORD - PUJ
1 stop9h 25mUnited Airlines
Mon 23/315:25PUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 10/1AED 1,458
Sun 26/408:45ORD - PUJ
Nonstop4h 42mUnited Airlines
Thu 30/413:50PUJ - ORD
Nonstop5h 09mUnited Airlines
Deal found 8/1AED 1,469
Tue 3/218:59ORD - PUJ
1 stop16h 08mDelta
Tue 10/217:46PUJ - ORD
1 stop18h 03mDelta
Deal found 8/1AED 1,480
Wed 15/405:49ORD - PUJ
1 stop8h 41mUnited Airlines
Wed 22/413:50PUJ - ORD
Nonstop5h 09mUnited Airlines
Deal found 10/1AED 1,487
Mon 16/314:30ORD - DXB
1 stop23h 15mAir India
Thu 26/309:55DXB - ORD
2 stops35h 35mAir India
Deal found 8/1AED 2,493

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 January 2026. 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

Sat 7/2

10:27-17:12

Nonstop4h 45m

Punta Cana

Tue 10/2

19:30-22:40

Nonstop5h 10m

AED 1,278

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 23/2

09:30-16:02

Nonstop4h 32m

Punta Cana

Thu 26/2

14:55-18:08

Nonstop5h 13m

AED 1,425

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 15/4

05:49-15:30

1 stop8h 41m

Punta Cana

Wed 22/4

13:50-17:59

Nonstop5h 09m

AED 1,487

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 10/2

07:00-16:21

1 stop7h 21m

Punta Cana

Fri 13/2

18:06-13:20

2 stops21h 14m

AED 1,495

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 8/4

08:45-14:27

Nonstop4h 42m

Punta Cana

Wed 15/4

13:50-17:59

Nonstop5h 09m

AED 1,506

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 1/2

09:30-16:02

Nonstop4h 32m

Punta Cana

Sun 8/2

14:55-18:08

Nonstop5h 13m

AED 1,517

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 23/3

17:50-12:40

1 stop17h 50m

Punta Cana

Tue 31/3

14:45-23:59

1 stop10h 14m

AED 1,524

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 22/3

19:14-13:53

1 stop17h 39m

Punta Cana

Tue 31/3

14:45-23:59

1 stop10h 14m

AED 1,524

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 28/4

08:45-14:27

Nonstop4h 42m

Punta Cana

Tue 5/5

13:50-17:59

Nonstop5h 09m

AED 1,535

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 30/3

17:59-12:08

2 stops17h 09m

Punta Cana

Thu 9/4

16:15-08:40

1 stop17h 25m

AED 1,539

Flights are sorted by cheapest return flights first.

Deals found on 10/1

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 2 January 2026.

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 23 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: United Airlines. This airline departs to the following popular destinations: Dubai.

Etihad Airways
Etihad Airways
From AED 3,011
United Airlines
United Airlines
From AED 2,443
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: New York (1,462 flights per day), Detroit (980 flights per day), and Toronto (802 flights per day).

Washington, D.C.
Washington, D.C.
From AED 545
Zurich
Zurich
From AED 2,747
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From AED 2,264
Dubai Intl
Dubai Intl
From AED 2,150

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Washington, D.C., with prices starting at AED 545. Explore other affordable destinations below.

Washington, D.C.
Washington, D.C.
From AED 545
Orlando
Orlando
From AED 789
Portland
Portland
From AED 1,059
Indianapolis
Indianapolis
From AED 1,248

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 United Airlines from Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,145 reviews
Check prices

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,145 reviews
United Airlines
7.4
Good
9,145 reviews
Check prices

Boarding

7.7

Food

6.6

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 10 January 2026.

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

    The most selected flight destinations from Chicago for the current month are Ahmedabad, Atlanta, Mumbai. While Atlanta, Boston, Ahmedabad 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 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 2,269 round trip
    Travel from Chicago to Sharjah from AED 2,710 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.