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£66+ 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 4/12. 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 — LHR
14 Dec — 21 Dec1
1 adult
1 adult, Economy, 0 bags

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 14 November 2025.

Cheapest airline

Frontier

Good round-trip deal

£44 or less

Good one-way deal

£38 or less
On average, Frontier currently has the cheapest one-way flight from Chicago (avg. price of £126).
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Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Find flights from Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 14 November 2025.

Mon 1/1218:30ORD - EDI
2 stops19h 45mMultiple Airlines
Fri 5/1206:45EDI - ORD
2 stops16h 35mMultiple Airlines
Deal found 14/11£345
Sun 11/118:30ORD - GLA
1 stop9h 25mIcelandair
Sun 18/112:35GLA - ORD
1 stop10h 45mIcelandair
Deal found 13/11£357
Mon 8/1218:30ORD - EDI
2 stops19h 45mMultiple Airlines
Fri 12/1206:45EDI - ORD
2 stops16h 35mMultiple Airlines
Deal found 12/11£369
Tue 3/218:30ORD - GLA
1 stop9h 25mIcelandair
Sat 7/212:35GLA - ORD
1 stop10h 45mIcelandair
Deal found 12/11£369
Mon 1/1218:30ORD - EDI
2 stops19h 20mMultiple Airlines
Tue 9/1208:20EDI - ORD
2 stops15h 00mMultiple Airlines
Deal found 12/11£369
Mon 1/1218:30ORD - GLA
1 stop9h 25mIcelandair
Fri 5/1212:35GLA - ORD
1 stop10h 45mIcelandair
Deal found 14/11£370
Sat 10/118:30ORD - GLA
1 stop9h 25mIcelandair
Sat 17/112:35GLA - ORD
1 stop10h 45mIcelandair
Deal found 12/11£372
Thu 5/218:30ORD - EDI
2 stops19h 10mMultiple Airlines
Thu 12/207:45EDI - ORD
2 stops15h 35mMultiple Airlines
Deal found 13/11£373
Sat 10/118:30ORD - GLA
1 stop9h 25mIcelandair
Mon 19/112:35GLA - ORD
1 stop10h 45mIcelandair
Deal found 13/11£376
Mon 1/1218:30ORD - EDI
2 stops19h 45mMultiple Airlines
Wed 10/1207:25EDI - ORD
2 stops15h 55mMultiple Airlines
Deal found 13/11£387
Sun 11/118:30ORD - GLA
1 stop9h 25mIcelandair
Fri 16/112:35GLA - ORD
1 stop10h 45mIcelandair
Deal found 13/11£390
Mon 5/118:30ORD - GLA
2 stops15h 30mMultiple Airlines
Mon 19/123:35GLA - ORD
2 stops23h 45mMultiple Airlines
Deal found 11/11£392

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 14 November 2025. In the last 7 days, Cheapflights users made a total of 858,174 searches

Fly to

Heathrow

Route

Depart

Return

Price

ChicagoGlasgow

ORD - GLA

ORDGLA

Chicago O'Hare Intl

Tue 3/2

18:30-09:55

1 stop9h 25m

Glasgow Intl

Sat 7/2

12:35-17:20

1 stop10h 45m

£369

ChicagoGlasgow

ORD - GLA

ORDGLA

Chicago O'Hare Intl

Wed 14/1

18:30-09:55

1 stop9h 25m

Glasgow Intl

Fri 23/1

12:35-17:20

1 stop10h 45m

£390

ChicagoGlasgow

ORD - GLA

ORDGLA

Chicago O'Hare Intl

Sun 11/1

18:30-09:55

1 stop9h 25m

Glasgow Intl

Fri 16/1

12:35-17:20

1 stop10h 45m

£390

ChicagoLondon

ORD - STN

ORDSTN

Chicago O'Hare Intl

Sun 8/2

19:10-23:25

3 stops22h 15m

London Stansted

Fri 13/2

19:50-16:45

2 stops26h 55m

£426

ChicagoLondon

MDW - LGW

MDWLGW

Chicago Midway

Thu 15/1

09:43-10:00

1 stop18h 17m

London Gatwick

Fri 23/1

14:00-08:33

2 stops24h 33m

£428

ChicagoLondon

ORD - LTN

ORDLTN

Chicago O'Hare Intl

Tue 2/12

18:30-20:05

2 stops19h 35m

London Luton

Thu 11/12

09:00-17:20

2 stops14h 20m

£445

ChicagoLondon

ORD - LHR

ORDLHR

Chicago O'Hare Intl

Tue 2/12

16:20-11:40

1 stop13h 20m

London Heathrow

Thu 11/12

08:40-18:27

2 stops15h 47m

£449

ChicagoLondon

MDW - LHR

MDWLHR

Chicago Midway

Tue 2/12

10:49-11:40

1 stop18h 51m

London Heathrow

Thu 11/12

11:45-23:47

2 stops18h 02m

£449

ChicagoLondon

MDW - LHR

MDWLHR

Chicago Midway

Tue 2/12

13:50-07:05

1 stop11h 15m

London Heathrow

Tue 16/12

11:05-18:18

1 stop13h 13m

£454

ChicagoLondon

MDW - LHR

MDWLHR

Chicago Midway

Wed 26/11

13:47-07:05

1 stop11h 18m

London Heathrow

Thu 18/12

08:55-16:31

1 stop13h 36m

£454

Flights are sorted by cheapest return flights first.

Deals found on 12/11

Showing 1-10 of 60 results
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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?

Use this chart to determine the optimal time to book a return flight from Chicago to Heathrow. Price data was last updated on 7 November 2025.

Booking 68 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, May is the cheapest month in which you can book a flight from Chicago (average of £298). Flying from Chicago in June will prove the most costly (average of £688). 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: British Airways, Iberia, Finnair, Aer Lingus, United Airlines. These airlines fly to the following popular destinations: London.

British Airways
British Airways
From £392
American Airlines
American Airlines
From £69
Iberia
Iberia
From £429
Aer Lingus
Aer Lingus
From £366

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 (1,565 flights per day), Detroit (1,104 flights per day) and Los Angeles (686 flights per day).

London
London
From £287
New York
New York
From £34
Dublin
Dublin
From £307
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From £582

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Palm Beach Intl, with prices starting at £22. Explore other affordable destinations below.

Palm Beach Intl
Palm Beach Intl
From £22
New York
New York
From £34
Dallas/Fort Worth
Dallas/Fort Worth
From £37
Houston Hobby
Houston Hobby
From £40

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 858,174 searches.
Check out reviews from past customers who have flown Iberia and British Airways from Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Iberia
7.0
Good
3,010 reviews
Check prices

Overall

7.0

Boarding

7.1

Entertainment

6.6

Food

6.3

Comfort

6.8

Crew

7.7

Reviews

1 / 20
6.0
Good

David,May 2025

JFK - MAD

Unfortunately carry on bag over head was full. I was seated 27J and had to place my carry on by seat 8 .. other then that it was a good flight
Iberia
7.0
Good
3,010 reviews
Iberia
7.0
Good
3,010 reviews
Check prices

Overall

7.0

Boarding

7.1

Entertainment

6.6

Food

6.3

Comfort

6.8

Crew

7.7

Reviews

1 / 20
6.0
Good

David,May 2025

JFK - MAD

Unfortunately carry on bag over head was full. I was seated 27J and had to place my carry on by seat 8 .. other then that it was a good flight
British Airways
6.7
Okay
7,516 reviews
Iberia
7.0
Good
3,010 reviews
Check prices

Overall

7.0

Boarding

7.1

Entertainment

6.6

Food

6.3

Comfort

6.8

Crew

7.7

Reviews

1 / 20
6.0
Good

David,May 2025

JFK - MAD

Unfortunately carry on bag over head was full. I was seated 27J and had to place my carry on by seat 8 .. other then that it was a good flight

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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 14 November 2025.

  • What are the most popular destinations to fly to from Chicago?

    This month, the top selected destinations from Chicago are Mumbai, Atlanta, Ahmedabad. Throughout the year, Atlanta, Boston, Ahmedabad are some of the top choices made by users flying from Chicago.

  • What is the cheapest airport to fly out of Chicago?

    Chicago O'Hare Intl airport offers the cheapest routes to Almaty, from £308; whereas Chicago Midway airport is typically cheaper if you're flying to London, from £379. It's best to make sure you are flexible on dates to find the cheapest possible flight options for your journey.

  • What are the cheapest airlines flying from Chicago to anywhere?

    Over the past few days, we've found that Frontier, Spirit Airlines, and Air Canada have the cheapest prices from Chicago. Frontier flights from Chicago to Atlanta Hartsfield-Jackson (£42), Spirit Airlines flights from Chicago to Miami (£51), and Air Canada flights from Chicago to Toronto (£112).

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently May; with June 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?

    Check out the cheapest flights from Chicago to embark to:
    Travel from Chicago to London from £308 round trip
    Travel from Chicago to Edinburgh from £347 round trip
    Travel from Chicago to Almaty from £964 round trip

  • How does Cheapflights help users find flights from Chicago?

    900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Chicago today with Cheapflights!

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

    Millions of users choose and trust Cheapflights to book the best flight deals from Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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

    Yes, we can. To see specific flights from Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

    Yes! Start tracking prices for flights from Chicago today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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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?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Chicago today with Cheapflights!

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

Millions of users choose and trust Cheapflights to book the best flight deals from Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Chicago with no change fees?

Yes, we can. To see specific flights from Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes! Start tracking prices for flights from Chicago today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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