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฿5,471+ 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 17/6. 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 — BKK
12 Jun — 19 Jun1
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 13 May 2026. In the last 7 days, Cheapflights users made a total of 17,341 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 29/6

06:00-16:20

1 stop13h 20m

Anchorage

Tue 7/7

23:15-08:29

Nonstop6h 14m

฿13,239

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 5/6

18:20-00:50

1 stop9h 30m

Anchorage

Mon 8/6

06:00-21:25

1 stop12h 25m

฿13,563

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sat 5/9

14:22-20:51

1 stop9h 29m

Anchorage

Sat 12/9

05:05-23:59

1 stop15h 54m

฿13,563

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 8/7

06:55-13:17

1 stop9h 22m

Anchorage

Thu 16/7

22:10-08:30

1 stop7h 20m

฿13,563

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Thu 10/9

13:35-00:33

2 stops13h 58m

Anchorage

Thu 17/9

01:30-17:22

1 stop12h 52m

฿13,725

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 3/7

17:55-23:56

1 stop9h 01m

Anchorage

Wed 8/7

01:30-18:57

2 stops14h 27m

฿13,790

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sat 11/7

18:25-00:59

1 stop9h 34m

Anchorage

Sun 19/7

01:30-18:57

2 stops14h 27m

฿13,790

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sat 20/6

12:46-23:56

2 stops14h 10m

Anchorage

Sun 28/6

01:30-18:58

2 stops14h 28m

฿13,951
Fastest return journey

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Tue 18/8

10:00-13:42

Nonstop6h 42m

Anchorage

Tue 25/8

22:26-07:40

Nonstop6h 14m

฿14,372

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Tue 18/8

10:00-13:42

Nonstop6h 42m

Anchorage

Mon 24/8

22:26-07:40

Nonstop6h 14m

฿14,372

Flights are sorted by cheapest return flights first.

Deals found on 8/5

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?

Booking 10 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago?

Currently, January is the cheapest month in which you can book a flight from Chicago (average of ฿26,576). Flying from Chicago in August will prove the most costly (average of ฿63,769). 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?

Many airlines operate round-trip flights from Chicago: ANA, Korean Air, EVA Air, Cathay Pacific. These airlines fly to the following popular destinations: Bangkok.

ANA
ANA
From ฿24,320
อลาสกาแอร์ไลน์
อลาสกาแอร์ไลน์
From ฿25,210
Korean Air
Korean Air
From ฿22,610
EVA Air
EVA Air
From ฿26,695

What are popular destinations to fly to from Chicago?

If you’re flying from Chicago, these routes are more frequently taken by airlines Detroit (1,452 flights per day), New York (1,232 flights per day) and Minneapolis (799 flights per day).

Seattle/Tacoma Intl
Seattle/Tacoma Intl
From ฿26,585
Boston Logan Intl
Boston Logan Intl
From ฿2,700
Dallas/Fort Worth
Dallas/Fort Worth
From ฿12,154
Tokyo
Tokyo
From ฿41,838

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Las Vegas Harry Reid Intl, with prices starting at ฿2,064. Explore other affordable destinations below.

Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From ฿2,064
Boston Logan Intl
Boston Logan Intl
From ฿2,700
Houston Hobby
Houston Hobby
From ฿3,321

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 17,341 searches.
Get a feel of what it's like to fly with ANA from Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
ANA
8.3
Very Good
1,208 reviews
Check prices

Entertainment

8.0

Food

7.7

Comfort

8.2

Boarding

8.5

Crew

8.7

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

EWR - NRT

Flights were on time and flew ahead of schedule. Seating was comfortable. Meal quality left a little to be desired, and service was mostly mechanical.
ANA
8.3
Very Good
1,208 reviews
ANA
8.3
Very Good
1,208 reviews
Check prices

Entertainment

8.0

Food

7.7

Comfort

8.2

Boarding

8.5

Crew

8.7

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

EWR - NRT

Flights were on time and flew ahead of schedule. Seating was comfortable. Meal quality left a little to be desired, and service was mostly mechanical.

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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 May 2026.

  • 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, Athens. While Boston, Atlanta, Ahmedabad are the top choices made by travellers year-round.

  • Which is the cheapest airport to catch a flight from Chicago?

    Chicago O'Hare Intl airport offers the cheapest routes to Bangkok, from ฿29,845; whereas Chicago Midway airport is typically cheaper if you're flying to Bangkok, from ฿31,593. It's best to make sure you are flexible on dates to find the cheapest possible flight options for your journey.

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently January; with August 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?

    Here are some of the cheapest flight destinations from Chicago:
    Fly from Chicago to Bangkok from ฿29,845

  • How does Cheapflights help users find flights from Chicago?

    Cheapflights helps you search for flights from Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

  • Why should you use Cheapflights to find cheap flight tickets from Chicago?

    Cheapflights helps you find that perfect flight from Chicago by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

  • Can Cheapflights find flights from Chicago with no change fees?

    Yes! Cheapflights helps users easily find flights from Chicago with no change fees.

  • Can Cheapflights notify me if prices for flights from Chicago become cheaper?

    Yes, Cheapflights has a feature called Price Alerts, which offers users the ability to be notified when flight prices change. Track prices for your flight from Chicago today and book when you’re ready!

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Fly with Cheapflights

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How does Cheapflights help users find flights from Chicago?

Cheapflights helps you search for flights from Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Chicago?

Cheapflights helps you find that perfect flight from Chicago by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from Chicago with no change fees.

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alerts, which offers users the ability to be notified when flight prices change. Track prices for your flight from Chicago today and book when you’re ready!

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