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AED 400+ 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 21/5. 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
10 May — 17 May1
1 adult
1 adult, Economy, 0 bags

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 April 2026. In the last 7 days, Cheapflights users made a total of 220,657 searches

Fly to

Route

Departure

Return

Price

Cheapest return flight
Fastest return journey

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 19/5

09:30-15:12

Nonstop4h 42m

Punta Cana

Fri 22/5

13:50-17:59

Nonstop5h 09m

AED 1,564

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 3/5

05:00-13:11

1 stop7h 11m

Punta Cana

Fri 8/5

13:50-17:59

Nonstop5h 09m

AED 1,623

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 27/4

07:10-14:32

1 stop6h 22m

Punta Cana

Sat 2/5

14:46-23:59

1 stop10h 13m

AED 1,858

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 1/5

20:32-14:24

1 stop16h 52m

Punta Cana

Mon 4/5

15:57-08:01

2 stops17h 04m

AED 1,935

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 3/8

08:45-14:27

Nonstop4h 42m

Punta Cana

Fri 7/8

13:50-17:59

Nonstop5h 09m

AED 2,244

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 8/8

06:30-15:49

1 stop8h 19m

Punta Cana

Thu 13/8

14:52-07:56

2 stops18h 04m

AED 2,255

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 27/4

08:45-14:27

Nonstop4h 42m

Punta Cana

Mon 4/5

13:50-17:59

Nonstop5h 09m

AED 2,313

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 27/7

08:45-14:27

Nonstop4h 42m

Punta Cana

Mon 3/8

13:50-17:59

Nonstop5h 09m

AED 2,328

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 20/6

12:12-17:57

Nonstop4h 45m

Punta Cana

Sun 28/6

18:00-22:10

Nonstop5h 10m

AED 2,479

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Sat 3/10

16:20-23:00

1 stop21h 40m

Dubai Intl

Fri 9/10

01:00-14:15

1 stop22h 15m

AED 2,739

Flights are sorted by cheapest return flights first.

Deals found on 9/4

Showing 1-10 of 60 resultsSorted by cheapest first
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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 3 April 2026.

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 68 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 2,056). Flying from Chicago in July will prove the most costly (average of AED 3,110). 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 2,480
United Airlines
United Airlines
From AED 2,443
Turkish Airlines
Turkish Airlines
From AED 2,016

What are popular destinations to fly to from Chicago?

Some of the most frequent flights departing from Chicago everyday are: Detroit (1,276 flights per day), New York (1,059 flights per day), and Los Angeles (680 flights per day).

Amman Queen Alia Intl
Amman Queen Alia Intl
From AED 2,064
Washington, D.C.
Washington, D.C.
From AED 545
Lisbon Humberto Delgado
Lisbon Humberto Delgado
From AED 2,189

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
9,562 reviews
Check prices

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

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
9,562 reviews
United Airlines
7.4
Good
9,562 reviews
Check prices

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

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

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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 10 April 2026.

  • 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, Austin. While Boston, Atlanta, 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 July 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 2,567 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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