Flights from London to Chicago (STN to MDW)

Discover more affordable routes and cheaper dates from London to Chicago (STN to MDW) within a date range.

⭐ Search by country or region to discover more affordable routes, like Netherlands → Italy or Europe → South East Asia.

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  • US$1288.68
    RyanairAer LingusFrontier Airlines
    6:30am - 4:21pm
    Sun Dec 1st 2024
    39h 51m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 203 Depart at 6:30am from London (STN) Fly for 1h 20m Arrive at 7:50am in Dublin (DUB)

    Layover in Dublin for 4h 30m

    Sun Dec 1st 2024 Aer Lingus · EI 141 Depart at 12:20pm from Dublin (DUB) Fly for 9h 40m Arrive at 5:00pm in Miami (MIA)

    Layover in Miami for 21h 8m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2109 Depart at 2:08pm from Miami (MIA) Fly for 3h 13m Arrive at 4:21pm in Chicago (MDW)

  • US$1305.43
    RyanairAer LingusFrontier Airlines
    8:15am - 4:21pm
    Sun Dec 1st 2024
    38h 6m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 210 Depart at 8:15am from London (STN) Fly for 1h 20m Arrive at 9:35am in Dublin (DUB)

    Layover in Dublin for 2h 45m

    Sun Dec 1st 2024 Aer Lingus · EI 141 Depart at 12:20pm from Dublin (DUB) Fly for 9h 40m Arrive at 5:00pm in Miami (MIA)

    Layover in Miami for 21h 8m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2109 Depart at 2:08pm from Miami (MIA) Fly for 3h 13m Arrive at 4:21pm in Chicago (MDW)

  • US$1476.79
    RyanairSASFrontier Airlines
    6:20am - 11:58pm
    Sun Dec 1st 2024
    23h 38m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 2618 Depart at 6:20am from London (STN) Fly for 1h 45m Arrive at 9:05am in Copenhagen (CPH)

    Layover in Copenhagen for 3h 55m

    Sun Dec 1st 2024 SAS · SK 929 Depart at 1:00pm from Copenhagen (CPH) Fly for 10h 10m Arrive at 5:10pm in Atlanta (ATL)

    Layover in Atlanta for 5h 50m

    Sun Dec 1st 2024 Frontier Airlines · F9 2291 Depart at 11:00pm from Atlanta (ATL) Fly for 1h 58m Arrive at 11:58pm in Chicago (MDW)

  • US$1476.79
    RyanairSASFrontier Airlines
    6:20am - 11:10am
    Sun Dec 1st 2024
    34h 50m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 2618 Depart at 6:20am from London (STN) Fly for 1h 45m Arrive at 9:05am in Copenhagen (CPH)

    Layover in Copenhagen for 3h 55m

    Sun Dec 1st 2024 SAS · SK 929 Depart at 1:00pm from Copenhagen (CPH) Fly for 10h 10m Arrive at 5:10pm in Atlanta (ATL)

    Layover in Atlanta for 16h 58m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2143 Depart at 10:08am from Atlanta (ATL) Fly for 2h 2m Arrive at 11:10am in Chicago (MDW)

  • US$1520.42
    RyanairTAP PortugalFrontier Airlines
    6:15am - 4:21pm
    Sun Dec 1st 2024
    40h 6m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 1080 Depart at 6:15am from London (STN) Fly for 2h 50m Arrive at 9:05am in Lisbon (LIS)

    Layover in Lisbon for 8h 20m

    Sun Dec 1st 2024 TAP Portugal · TP 225 Depart at 5:25pm from Lisbon (LIS) Fly for 9h 35m Arrive at 10:00pm in Miami (MIA)

    Layover in Miami for 16h 8m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2109 Depart at 2:08pm from Miami (MIA) Fly for 3h 13m Arrive at 4:21pm in Chicago (MDW)

  • US$1527.86
    RyanairTAP PortugalFrontier Airlines
    9:40am - 4:21pm
    Sun Dec 1st 2024
    36h 41m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 1882 Depart at 9:40am from London (STN) Fly for 2h 50m Arrive at 12:30pm in Lisbon (LIS)

    Layover in Lisbon for 4h 55m

    Sun Dec 1st 2024 TAP Portugal · TP 225 Depart at 5:25pm from Lisbon (LIS) Fly for 9h 35m Arrive at 10:00pm in Miami (MIA)

    Layover in Miami for 16h 8m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2109 Depart at 2:08pm from Miami (MIA) Fly for 3h 13m Arrive at 4:21pm in Chicago (MDW)

  • US$1532
    PlayPlayFrontier Airlines
    11:00am - 5:01pm
    Sun Dec 1st 2024
    36h 1m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Play · OG 801 Depart at 11:00am from London (STN) Fly for 3h 5m Arrive at 2:05pm in Reykjavik (KEF)

    Layover in Reykjavik for 1h 15m

    Sun Dec 1st 2024 Play · OG 101 Depart at 3:20pm from Reykjavik (KEF) Fly for 6h 40m Arrive at 5:00pm in Washington, D.C. (BWI)

    Layover in Washington, D.C. for 23h 0m

    Mon Dec 2nd 2024 Frontier Airlines · F9 3087 Depart at 4:00pm from Washington, D.C. (BWI) Fly for 2h 1m Arrive at 5:01pm in Chicago (MDW)

  • US$1553
    RyanairTAP PortugalFrontier Airlines
    11:35am - 4:21pm
    Sun Dec 1st 2024
    34h 46m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 1884 Depart at 11:35am from London (STN) Fly for 2h 50m Arrive at 2:25pm in Lisbon (LIS)

    Layover in Lisbon for 3h 0m

    Sun Dec 1st 2024 TAP Portugal · TP 225 Depart at 5:25pm from Lisbon (LIS) Fly for 9h 35m Arrive at 10:00pm in Miami (MIA)

    Layover in Miami for 16h 8m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2109 Depart at 2:08pm from Miami (MIA) Fly for 3h 13m Arrive at 4:21pm in Chicago (MDW)

  • US$1649.13
    RyanairVirgin Atlantic AirwaysVirgin Atlantic Airways
    8:45am - 9:46pm
    Sun Dec 1st 2024
    43h 1m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 8230 Depart at 8:45am from London (STN) Fly for 2h 10m Arrive at 11:55am in Barcelona (BCN)

    Layover in Barcelona for 23h 0m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 3937 Depart at 10:55am from Barcelona (BCN) Fly for 10h 25m Arrive at 3:20pm in Atlanta (ATL)

    Layover in Atlanta for 5h 30m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 2617 Depart at 8:50pm from Atlanta (ATL) Fly for 1h 56m Arrive at 9:46pm in Chicago (MDW)

  • US$1650.26
    RyanairVirgin Atlantic AirwaysVirgin Atlantic Airways
    11:10am - 9:46pm
    Sun Dec 1st 2024
    40h 36m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 9014 Depart at 11:10am from London (STN) Fly for 2h 10m Arrive at 2:20pm in Barcelona (BCN)

    Layover in Barcelona for 20h 35m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 3937 Depart at 10:55am from Barcelona (BCN) Fly for 10h 25m Arrive at 3:20pm in Atlanta (ATL)

    Layover in Atlanta for 5h 30m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 2617 Depart at 8:50pm from Atlanta (ATL) Fly for 1h 56m Arrive at 9:46pm in Chicago (MDW)

  • US$1665.57
    RyanairVirgin Atlantic AirwaysVirgin Atlantic Airways
    9:55pm - 9:46pm
    Sun Dec 1st 2024
    29h 51m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 9810 Depart at 9:55pm from London (STN) Fly for 2h 10m Arrive at 1:05am in Barcelona (BCN)

    Layover in Barcelona for 9h 50m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 3937 Depart at 10:55am from Barcelona (BCN) Fly for 10h 25m Arrive at 3:20pm in Atlanta (ATL)

    Layover in Atlanta for 5h 30m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 2617 Depart at 8:50pm from Atlanta (ATL) Fly for 1h 56m Arrive at 9:46pm in Chicago (MDW)

  • US$1705.27
    RyanairVirgin Atlantic AirwaysVirgin Atlantic Airways
    7:15pm - 9:46pm
    Sun Dec 1st 2024
    32h 31m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 9815 Depart at 7:15pm from London (STN) Fly for 2h 10m Arrive at 10:25pm in Barcelona (BCN)

    Layover in Barcelona for 12h 30m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 3937 Depart at 10:55am from Barcelona (BCN) Fly for 10h 25m Arrive at 3:20pm in Atlanta (ATL)

    Layover in Atlanta for 5h 30m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 2617 Depart at 8:50pm from Atlanta (ATL) Fly for 1h 56m Arrive at 9:46pm in Chicago (MDW)

  • US$1707.43
    RyanairVirgin Atlantic AirwaysVirgin Atlantic Airways
    2:55pm - 9:46pm
    Sun Dec 1st 2024
    36h 51m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 9044 Depart at 2:55pm from London (STN) Fly for 2h 10m Arrive at 6:05pm in Barcelona (BCN)

    Layover in Barcelona for 16h 50m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 3937 Depart at 10:55am from Barcelona (BCN) Fly for 10h 25m Arrive at 3:20pm in Atlanta (ATL)

    Layover in Atlanta for 5h 30m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 2617 Depart at 8:50pm from Atlanta (ATL) Fly for 1h 56m Arrive at 9:46pm in Chicago (MDW)

  • US$1760.36
    RyanairVirgin Atlantic AirwaysVirgin Atlantic Airways
    12:05pm - 9:46pm
    Sun Dec 1st 2024
    39h 41m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 5998 Depart at 12:05pm from London (STN) Fly for 2h 30m Arrive at 3:35pm in Madrid (MAD)

    Layover in Madrid for 19h 25m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 3890 Depart at 11:00am from Madrid (MAD) Fly for 10h 20m Arrive at 3:20pm in Atlanta (ATL)

    Layover in Atlanta for 5h 30m

    Mon Dec 2nd 2024 Virgin Atlantic Airways · VS 2617 Depart at 8:50pm from Atlanta (ATL) Fly for 1h 56m Arrive at 9:46pm in Chicago (MDW)

  • US$2345.81
    RyanairSASFrontier Airlines
    6:20am - 11:58pm
    Sun Dec 1st 2024
    23h 38m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 2618 Depart at 6:20am from London (STN) Fly for 1h 45m Arrive at 9:05am in Copenhagen (CPH)

    Layover in Copenhagen for 3h 55m

    Sun Dec 1st 2024 SAS · SK 929 Depart at 1:00pm from Copenhagen (CPH) Fly for 10h 10m Arrive at 5:10pm in Atlanta (ATL)

    Layover in Atlanta for 5h 50m

    Sun Dec 1st 2024 Frontier Airlines · F9 2291 Depart at 11:00pm from Atlanta (ATL) Fly for 1h 58m Arrive at 11:58pm in Chicago (MDW)

  • US$2853.13
    RyanairBritish AirwaysFrontier Airlines
    9:35am - 1:15am
    Sun Dec 1st 2024
    21h 40m
    London (STN) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Ryanair · FR 5996 Depart at 9:35am from London (STN) Fly for 2h 30m Arrive at 1:05pm in Madrid (MAD)

    Layover in Madrid for 2h 55m

    Sun Dec 1st 2024 British Airways · BA 4299 Depart at 4:00pm from Madrid (MAD) Fly for 11h 35m Arrive at 8:35pm in Dallas (DFW)

    Layover in Dallas for 2h 24m

    Sun Dec 1st 2024 Frontier Airlines · F9 2882 Depart at 10:59pm from Dallas (DFW) Fly for 2h 16m Arrive at 1:15am in Chicago (MDW)

@sarahbb1
Sarah Belizaire
@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

@eyupitsjohn
John Ford
@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

@oamingsonaa
Roaming Sonaa
@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality.

@andy_travels
Andy Travels
@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

@travelwitbender
Travel With Bender
@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

@travel.with.wes
Wesley Mergard
@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Explore Flight Options

FlightList Blog

Flightlist Interviews 7 Travel Experts On Why They Book One Way Flights
Flightlist Interviews 7 Travel Experts On Why They Book One Way Flights
Why I built FlightList & solved my own problem
Why I Built FlightList & Solved My Own Problem

About FlightList

❝Founded by a remote worker and frequent flyer, who discovered that the best deals come from searching with flexible dates across entire countries or regions. Our streamlined platform strips away the clutter found on typical travel sites, offering a clean interface that focuses solely on finding cost-effective flights. Unlike traditional booking sites, FlightList allows users to search by date ranges and broad destinations, unveiling opportunities that rigid parameters often miss. Our filters let travelers tailor searches to their specific needs, whether they're digital nomads seeking their next adventure or budget-conscious explorers maximizing travel funds. We've made finding cheap flights into a quicker and easier experience, empowering users to discover just how far their budget can take them.❞

- Hans Desjarlais, Founder Hans Desjarlais Profile Picture