Cheap flights from Wales to Chicago from £651
This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 18/11. Fares are subject to change and may not be available on all flights or dates of travel.
Cheap flight deals from Wales to Chicago
Cheapest flights from Wales to ChicagoExplore the most affordable flight options available from Wales to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 5 October 2026.
Explore the most affordable flight options available from Wales to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 5 October 2026.
Best flights from Wales to ChicagoDiscover carefully curated flight deals from Wales to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 5 October 2026.
Discover carefully curated flight deals from Wales to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 5 October 2026.
Last-minute flights from Wales to ChicagoDiscover last-minute flight deals from Wales to Chicago. Data last updated 5 October 2026 and is based on user searches.
Discover last-minute flight deals from Wales to Chicago. Data last updated 5 October 2026 and is based on user searches.
Cheapflights Fare Finder
Use the filters below to find and compare flights from Wales to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
CardiffChicago
CWL Cardiff Wales - ORD Chicago O'Hare Intl
CWLORD
Cardiff Wales
Wed 18/11
10:20-23:54
2 stops19h 34m
Chicago O'Hare Intl
Wed 25/11
12:38-09:45
2 stops15h 07m
CardiffChicago
CWL Cardiff Wales - ORD Chicago O'Hare Intl
CWLORD
Cardiff Wales
Mon 2/11
17:30-16:32
2 stops29h 02m
Chicago O'Hare Intl
Mon 9/11
13:35-09:45
2 stops14h 10m
CardiffChicago
CWL Cardiff Wales - ORD Chicago O'Hare Intl
CWLORD
Cardiff Wales
Mon 2/11
17:30-17:20
3 stops29h 50m
Chicago O'Hare Intl
Mon 9/11
18:30-09:50
3 stops33h 20m
CardiffChicago
CWL Cardiff Wales - ORD Chicago O'Hare Intl
CWLORD
Cardiff Wales
Wed 28/10
17:30-15:10
2 stops26h 40m
Chicago O'Hare Intl
Fri 30/10
16:55-07:50
1 stop9h 55m
CardiffChicago
CWL Cardiff Wales - ORD Chicago O'Hare Intl
CWLORD
Cardiff Wales
Mon 16/11
08:35-18:20
1 stop15h 45m
Chicago O'Hare Intl
Wed 18/11
15:55-13:00
1 stop15h 05m
CardiffChicago
CWL Cardiff Wales - ORD Chicago O'Hare Intl
CWLORD
Cardiff Wales
Tue 17/11
17:30-18:20
2 stops30h 50m
Chicago O'Hare Intl
Tue 24/11
15:55-08:30
3 stops34h 35m
CardiffChicago
CWL Cardiff Wales - ORD Chicago O'Hare Intl
CWLORD
Cardiff Wales
Fri 11/12
16:05-17:20
2 stops31h 15m
Chicago O'Hare Intl
Sat 19/12
20:05-08:10
1 stop30h 05m
Best time to book a flight from Wales to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Wales with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Wales to Chicago
Related info for your journey
Find useful and relevant information for your journey from Wales to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Wales to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 5 October 2026.
Complete your trip
Complete your trip to Chicago by adding a car hire and/or hotel booking to your travel itinerary.
Direct flights to Illinois
Book a non-stop flight to one of these other cities located in Illinois.
Search flights from Wales to Chicago by cabin class
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Wales and Chicago flights
Browse other Wales and Chicago flight options. Last updated on 5 October 2026.
Popular flight searches
Check out other popular destinations found by fellow travellers in 2026
Top airline flying from Wales to Chicago
Discover the top airline that operate flights from Wales to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated 5 October 2026.
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How does Cheapflights help users find flights from Wales to Chicago?
Deals for Wales to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.
Why should you use Cheapflights to find cheap flight tickets from Wales to Chicago?
Cheapflights simply makes it quick and affordable to book flights from Wales to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Can Cheapflights find flights from Wales to Chicago with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Wales to Chicago flexibly with Cheapflights today.
Can Cheapflights notify me if prices for flights from Wales to Chicago become cheaper?
Of course! You can now track prices for flights from Wales to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.