฿6,086+ 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 21/8. 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
29 Jul — 5 Aug1
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 29 June 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

Thu 20/8

10:50-21:29

1 stop13h 39m

Anchorage

Mon 24/8

21:20-06:32

Nonstop6h 12m

฿13,402

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 21/9

17:44-00:32

1 stop9h 48m

Anchorage

Mon 28/9

06:00-19:33

1 stop10h 33m

฿13,735

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 10/8

17:57-00:59

1 stop10h 02m

Anchorage

Wed 12/8

01:32-13:23

1 stop8h 51m

฿13,735

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Tue 1/9

06:00-14:13

1 stop11h 13m

Anchorage

Tue 15/9

15:30-05:01

1 stop10h 31m

฿13,735

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 10/8

17:57-00:59

1 stop10h 02m

Anchorage

Thu 20/8

11:01-23:29

1 stop9h 28m

฿13,735
Fastest return journey

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Thu 20/8

12:54-20:12

1 stop10h 18m

Anchorage

Sun 23/8

00:39-11:59

1 stop8h 20m

฿13,735

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Thu 1/10

07:00-16:28

1 stop12h 28m

Anchorage

Sun 4/10

22:10-11:39

1 stop10h 29m

฿13,735

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Tue 27/10

06:00-17:28

2 stops14h 28m

Anchorage

Thu 29/10

16:59-06:20

1 stop10h 21m

฿13,901

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 21/8

14:00-23:55

2 stops12h 55m

Anchorage

Thu 27/8

00:39-18:19

1 stop14h 40m

฿13,901

ChicagoChiang Mai

MDW - CNX

MDWCNX

Chicago Midway

Tue 3/11

17:15-22:55

2 stops40h 40m

Chiang Mai

Tue 17/11

00:15-22:10

2 stops34h 55m

฿31,394

Flights are sorted by cheapest return flights first.

Deals found on 24/6

Showing 1-10 of 60 resultsSorted by cheapest first
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.

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

Currently, July is the cheapest month in which you can book a flight from Chicago (average of ฿20,253). Flying from Chicago in September will prove the most costly (average of ฿82,908). 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 ฿24,986
อลาสกาแอร์ไลน์
อลาสกาแอร์ไลน์
From ฿25,900
Korean Air
Korean Air
From ฿23,229
EVA Air
EVA Air
From ฿27,426

What are popular destinations to fly to from Chicago?

If you’re flying from Chicago, these routes are more frequently taken by airlines Detroit (1,230 flights per day), New York (1,190 flights per day) and Los Angeles (827 flights per day).

Seattle/Tacoma Intl
Seattle/Tacoma Intl
From ฿27,313
Doha Hamad Intl
Doha Hamad Intl
From ฿19,322
Dallas/Fort Worth
Dallas/Fort Worth
From ฿12,487

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 ฿2,120. Explore other affordable destinations below.

Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From ฿2,120
Houston Hobby
Houston Hobby
From ฿3,412
Raleigh-Durham
Raleigh-Durham
From ฿10,873

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.

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.

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 29 June 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, Amman Queen Alia Intl Airport, Atlanta. While Atlanta, Boston, 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 ฿30,230; whereas Chicago Midway airport is typically cheaper if you're flying to Bangkok, from ฿30,596. 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 July; with September 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 ฿30,230

  • 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!

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?

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!

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.