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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 27/1. 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 — LHR
14 Feb — 21 Feb1
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 15 January 2026.

Cheapest airline

Spirit Airlines

Good round-trip deal

£43 or less

Good one-way deal

£26 or less
On average, Spirit Airlines currently has the cheapest one-way flight from Chicago (avg. price of £148).
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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 15 January 2026.

Mon 2/318:30
ORD
-
EDI
1 stop9h 30m
Icelandair
Tue 17/311:00
EDI
-
ORD
1 stop12h 20m
Icelandair
Deal found 13/1£361
Tue 17/319:30
ORD
-
GLA
1 stop9h 25m
Icelandair
Tue 24/312:35
GLA
-
ORD
1 stop10h 45m
Icelandair
Deal found 14/1£362
Wed 11/218:30
ORD
-
EDI
2 stops16h 45m
Multiple Airlines
Wed 18/207:25
EDI
-
ORD
2 stops15h 55m
Multiple Airlines
Deal found 14/1£365
Mon 2/218:30
ORD
-
EDI
1 stop9h 30m
Icelandair
Tue 10/211:00
EDI
-
ORD
1 stop12h 20m
Icelandair
Deal found 13/1£365
Tue 3/218:30
ORD
-
GLA
1 stop9h 25m
Icelandair
Sat 7/212:35
GLA
-
ORD
1 stop10h 45m
Icelandair
Deal found 13/1£366
Fri 6/218:30
ORD
-
EDI
2 stops20h 35m
Multiple Airlines
Mon 9/222:30
EDI
-
ORD
2 stops24h 50m
Multiple Airlines
Deal found 13/1£367
Tue 24/218:30
ORD
-
GLA
1 stop9h 25m
Icelandair
Mon 9/312:35
GLA
-
ORD
1 stop10h 45m
Icelandair
Deal found 15/1£370
Thu 5/218:30
ORD
-
GLA
2 stops20h 55m
Multiple Airlines
Mon 9/223:35
GLA
-
ORD
2 stops23h 45m
Multiple Airlines
Deal found 14/1£372
Sat 4/419:25
ORD
-
EDI
1 stop11h 55m
Icelandair
Thu 9/414:15
EDI
-
ORD
1 stop10h 00m
Icelandair
Deal found 13/1£373
Mon 2/318:30
ORD
-
GLA
1 stop9h 25m
Icelandair
Tue 17/312:35
GLA
-
ORD
1 stop10h 45m
Icelandair
Deal found 13/1£374
Thu 5/218:30
ORD
-
EDI
2 stops22h 00m
Multiple Airlines
Mon 9/222:30
EDI
-
ORD
2 stops24h 50m
Multiple Airlines
Deal found 12/1£376
Fri 17/419:25
ORD
-
GLA
1 stop12h 00m
Icelandair
Fri 24/414:20
GLA
-
ORD
1 stop13h 05m
Icelandair
Deal found 13/1£378

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 15 January 2026. 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

Sun 26/4

22:25-13:25

1 stop9h 00m

Glasgow Intl

Sat 9/5

14:20-18:15

1 stop9h 55m

£385

ChicagoLondon

ORD - STN

ORDSTN

Chicago O'Hare Intl

Mon 9/2

21:50-21:20

2 stops17h 30m

London Stansted

Mon 16/2

21:45-18:25

2 stops26h 40m

£392

ChicagoLondon

ORD - LGW

ORDLGW

Chicago O'Hare Intl

Wed 4/3

15:50-10:00

1 stop12h 10m

London Gatwick

Tue 10/3

08:50-18:55

1 stop15h 05m

£395

ChicagoLondon

ORD - STN

ORDSTN

Chicago O'Hare Intl

Mon 13/4

15:45-07:50

1 stop10h 05m

London Stansted

Wed 22/4

08:30-19:15

1 stop16h 45m

£402

ChicagoLondon

ORD - STN

ORDSTN

Chicago O'Hare Intl

Wed 28/1

21:50-21:05

2 stops17h 15m

London Stansted

Tue 3/2

06:30-19:45

3 stops19h 15m

£415

ChicagoGlasgow

ORD - GLA

ORDGLA

Chicago O'Hare Intl

Wed 25/2

17:10-12:50

1 stop13h 40m

Glasgow Intl

Mon 16/3

20:25-14:50

1 stop23h 25m

£417

ChicagoGlasgow

ORD - GLA

ORDGLA

Chicago O'Hare Intl

Sun 22/2

18:30-09:55

1 stop9h 25m

Glasgow Intl

Wed 18/3

12:35-18:20

1 stop10h 45m

£417

ChicagoGlasgow

ORD - GLA

ORDGLA

Chicago O'Hare Intl

Wed 25/2

16:01-12:50

2 stops14h 49m

Glasgow Intl

Thu 12/3

06:35-14:50

1 stop13h 15m

£420

ChicagoGlasgow

ORD - GLA

ORDGLA

Chicago O'Hare Intl

Wed 25/2

16:10-12:50

2 stops14h 40m

Glasgow Intl

Thu 19/3

12:45-19:45

1 stop12h 00m

£420

ChicagoGlasgow

ORD - GLA

ORDGLA

Chicago O'Hare Intl

Tue 24/2

16:10-13:05

2 stops14h 55m

Glasgow Intl

Thu 19/3

09:55-19:45

1 stop14h 50m

£420

Flights are sorted by cheapest return flights first.

Deals found on 13/1

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 9 January 2026.

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 £292). Flying from Chicago in June will prove the most costly (average of £667). 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, Aer Lingus, Finnair, United Airlines. These airlines fly to the following popular destinations: London.

British Airways
British Airways
From £384
American Airlines
American Airlines
From £68
Aer Lingus
Aer Lingus
From £341
Iberia
Iberia
From £426

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 (1,406 flights per day), Detroit (892 flights per day) and Toronto (790 flights per day).

London
London
From £206
Frankfurt am Main
Frankfurt am Main
From £199
Istanbul
Istanbul
From £365
Dublin
Dublin
From £204

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 £21. Explore other affordable destinations below.

Palm Beach Intl
Palm Beach Intl
From £21
Fort Lauderdale
Fort Lauderdale
From £25
Dallas/Fort Worth
Dallas/Fort Worth
From £29
Boston Logan Intl
Boston Logan Intl
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
3,087 reviews
Check prices

Entertainment

6.6

Food

6.4

Overall

7.0

Boarding

7.1

Comfort

6.7

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
3,087 reviews
Iberia
7.0
Good
3,087 reviews
Check prices

Entertainment

6.6

Food

6.4

Overall

7.0

Boarding

7.1

Comfort

6.7

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
7,674 reviews
Iberia
7.0
Good
3,087 reviews
Check prices

Entertainment

6.6

Food

6.4

Overall

7.0

Boarding

7.1

Comfort

6.7

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 15 January 2026.

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

    This month, the top selected destinations from Chicago are Ahmedabad, Atlanta, Mumbai. 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 £305; whereas Chicago Midway airport is typically cheaper if you're flying to London, from £439. 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 Spirit Airlines, Frontier, and American Airlines have the cheapest prices from Chicago. Spirit Airlines flights from Chicago to Miami (£50), Frontier flights from Chicago to Atlanta Hartsfield-Jackson (£77), and American Airlines flights from Chicago to London (£118).

  • 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 £305 round trip
    Travel from Chicago to Glasgow from £315 round trip
    Travel from Chicago to Edinburgh from £319 round trip
    Travel from Chicago to Manchester from £353 round trip
    Travel from Chicago to Almaty from £944 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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