฿3,313+ 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 11/1. 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 — BKK
10 Nov — 17 Nov1
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 11 October 2026. In the last 7 days, Cheapflights users made a total of 7,457,451 searches
Fly to
Route
Depart
Return
Cheapest return flight
ChicagoLouisville
ORD Chicago O'Hare Intl - SDF Louisville Intl
ORDSDF
Chicago O'Hare Intl
Mon 11/1
15:50-18:29
Nonstop1h 39m
Louisville Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
฿3,313
ChicagoLouisville
ORD Chicago O'Hare Intl - SDF Louisville Intl
ORDSDF
Chicago O'Hare Intl
Wed 4/11
18:10-20:52
Nonstop1h 42m
Louisville Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
฿3,480
ChicagoLouisville
ORD Chicago O'Hare Intl - SDF Louisville Intl
ORDSDF
Chicago O'Hare Intl
Tue 3/11
06:30-14:41
1 stop7h 11m
Louisville Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
฿3,648
ChicagoLouisville
ORD Chicago O'Hare Intl - SDF Louisville Intl
ORDSDF
Chicago O'Hare Intl
Mon 14/12
11:39-17:18
1 stop4h 39m
Louisville Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
฿3,648
ChicagoLouisville
ORD Chicago O'Hare Intl - SDF Louisville Intl
ORDSDF
Chicago O'Hare Intl
Fri 11/12
18:16-00:09
1 stop4h 53m
Louisville Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
฿3,648
ChicagoLas Vegas
ORD Chicago O'Hare Intl - LAS Las Vegas Harry Reid Intl
ORDLAS
Chicago O'Hare Intl
Sat 27/2
14:30-21:01
1 stop8h 31m
Las Vegas Harry Reid Intl
Wed 31/12
00:00-02:00
Nonstop0h 00m
฿3,681
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 24/11
06:00-14:21
1 stop7h 21m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
฿3,715
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 6/1
12:55-19:08
1 stop5h 13m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
฿3,715
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 5/12
18:16-01:15
1 stop5h 59m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
฿3,715
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 14/11
08:04-17:04
1 stop8h 00m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
฿3,715
Showing 1-10 of 60 resultsSorted by cheapest first
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.
CHI-BKK
ORD-SDF
ORD-BOS
ORD-LAS
ORD-PHX
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.
CHI-BKK
ORD-SDF
ORD-BOS
ORD-LAS
ORD-PHX
What is the cheapest month to book a flight from Chicago?
Currently, February is the cheapest month in which you can book a flight from Chicago (average of ฿29,683). Flying from Chicago in December will prove the most costly (average of ฿45,578). 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: Korean Air, EVA Air, Cathay Pacific. These airlines fly to the following popular destinations: Bangkok.
What are popular destinations to fly to from Chicago?
If you’re flying from Chicago, these routes are more frequently taken by airlines New York (1,239 flights per day), Detroit (1,198 flights per day) and Los Angeles (914 flights per day).
What is the cheapest place to fly to from Chicago?
The cheapest city to fly to from Chicago is Houston Hobby, with prices starting at ฿3,433. Explore other affordable destinations below.
When is the best time to book a flight from Chicago?
Booking 86 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
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Airports servicing Chicago
Fly out of one of these airports located in Chicago.
Fly from other United States cities
Consider departing from one of these cities also located in United States. Flight origins are based on user searches made on Cheapflights and were last updated on 11 October 2026.
Popular flight searches
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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 11 October 2026.
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Why should you use Cheapflights to find cheap flight tickets from Chicago?
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Yes! Cheapflights helps users easily find flights from Chicago with no change fees.
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