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฿5,549+ 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 7/7. 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
25 Jun — 2 Jul1
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 26 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

Thu 13/8

00:59-04:41

Nonstop6h 42m

Anchorage

Sun 16/8

01:22-05:00

1 stop24h 38m

฿12,949

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Tue 7/7

06:55-16:25

1 stop12h 30m

Anchorage

Sun 12/7

01:30-18:57

2 stops14h 27m

฿12,981

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Thu 25/6

08:36-00:55

1 stop19h 19m

Anchorage

Sun 28/6

01:30-18:58

2 stops14h 28m

฿12,981

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Tue 11/8

12:29-23:24

2 stops13h 55m

Anchorage

Wed 19/8

06:00-20:22

2 stops11h 22m

฿13,143
Fastest return journey

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Sat 29/8

07:20-11:12

Nonstop6h 52m

Anchorage

Tue 1/9

22:28-07:40

Nonstop6h 12m

฿13,176

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Wed 12/8

13:00-23:55

1 stop13h 55m

Anchorage

Sun 16/8

22:37-16:24

1 stop14h 47m

฿13,176

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Fri 14/8

12:29-23:55

2 stops14h 26m

Anchorage

Sat 22/8

22:08-16:24

2 stops15h 16m

฿13,565

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Tue 21/7

06:55-13:17

1 stop9h 22m

Anchorage

Sun 26/7

22:30-16:23

1 stop14h 53m

฿14,085

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 22/6

08:52-21:16

1 stop15h 24m

Anchorage

Tue 30/6

01:30-18:58

2 stops14h 28m

฿14,214

ChicagoAnchorage

ORD - ANC

ORDANC

Chicago O'Hare Intl

Mon 22/6

08:52-20:52

2 stops15h 00m

Anchorage

Thu 2/7

01:30-18:58

2 stops14h 28m

฿14,377

Flights are sorted by cheapest return flights first.

Deals found on 25/5

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.

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

Currently, August is the cheapest month in which you can book a flight from Chicago (average of ฿19,439). Flying from Chicago in July will prove the most costly (average of ฿73,830). 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 ฿24,383
อลาสกาแอร์ไลน์
อลาสกาแอร์ไลน์
From ฿25,274
Korean Air
Korean Air
From ฿22,668
EVA Air
EVA Air
From ฿26,763

What are popular destinations to fly to from Chicago?

If you’re flying from Chicago, these routes are more frequently taken by airlines Detroit (1,404 flights per day), New York (1,233 flights per day) and Los Angeles (798 flights per day).

Seattle/Tacoma Intl
Seattle/Tacoma Intl
From ฿26,654
Boston Logan Intl
Boston Logan Intl
From ฿2,707
Dallas/Fort Worth
Dallas/Fort Worth
From ฿12,185

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 ฿2,069. Explore other affordable destinations below.

Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From ฿2,069
Boston Logan Intl
Boston Logan Intl
From ฿2,707
Houston Hobby
Houston Hobby
From ฿3,329

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.

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
1,215 reviews
Check prices

Food

7.7

Entertainment

8.0

Overall

8.3

Comfort

8.2

Boarding

8.5

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

IAH - HND

Outstanding service on board. Loved that we got to use Polaris Lounge at IAH. On time and terrific trip.
ANA
8.3
Very Good
1,215 reviews
ANA
8.3
Very Good
1,215 reviews
Check prices

Food

7.7

Entertainment

8.0

Overall

8.3

Comfort

8.2

Boarding

8.5

Crew

8.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

IAH - HND

Outstanding service on board. Loved that we got to use Polaris Lounge at IAH. On time and terrific trip.

Browse thousands of different options on Cheapflights for your next trip

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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 26 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 Atlanta, Boston, 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 ฿29,792; whereas Chicago Midway airport is typically cheaper if you're flying to Bangkok, from ฿29,922. 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 August; 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?

    Here are some of the cheapest flight destinations from Chicago:
    Fly from Chicago to Bangkok from ฿29,792

  • 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

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!

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