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Planning a trip from Chicago to London? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.
For those planning a trip from Chicago to London, there are several ways to potentially save on flight costs. Generally, Wednesday is the cheapest day of the week to fly, while February is the cheapest month.
Cheapest Route: Opt for flights from Chicago O'Hare to London Heathrow for the most affordable route.
Booking Advance: Book your flight around 134 days in advance for the best prices.
Cheapest Airline: Consider flying with Icelandair, as it tends to offer the cheapest fares.
Layovers: Flights with one stop are generally cheaper than direct flights.
This feature is powered by ChatGPT: an OpenAI-developed artificial intelligence model trained with KAYAK proprietary data and third-party data not verified by KAYAK.
Low season | February |
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High season | March |
Cheapest flight | $196 |
Find which airlines fly direct from Chicago to London, which days they fly and book direct flights.
Direct departures
Chicago to London
Monday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Tuesday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Wednesday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Thursday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Friday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Saturday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Sunday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Direct returns
London to Chicago
Monday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Tuesday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Wednesday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Thursday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Friday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Saturday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
Sunday
American Airlines, British Airways, United Airlines
American Airlines, British Airways, +1 more
A bit rush for transit. Food and entertainment are not available
A bit rush for transit. Food and entertainment are not available
Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.
Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.
I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful
They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal
My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.
Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours
The flight was heavily booked so boarding was a lengthy process. The FA’s were rather abrupt during this process but became more gracious as the flight went on. Breakfast (puffed pastry and chewy sausage) was pretty horrible but there was fruit and yogurt which they didn’t mess up. Overall it was fine.
Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service
Our seats were all the way in back of the plane,
really bad they refused to check in luggages that I had purchased, even showing them the transaction receipt from british airways app the staff in miami was MEDIOCRE
Crew was great and responsive. Entertainment quit working with about 4 hours remaining on the flight. My seat cushion was broken.
Not very good , the stewardess were unfriendly and they don't like to be bothered. Cos was a night flight and they need to sleep.
British Airways staff are very polite and willing to help.
I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude
Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!
Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.
This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable
Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.
You were more on time than United. I'm so over united delays.
For an economy lite experience, it's by far the best I've had. New planes, clean, great destinations. Very happy to have discovered Iceland Air.
Smooth efficient airline. Think they should have their own bag drop as the queue took 30mins to bmscan and drop
No food was served for 7.5 hrs flight. When our flight changed to other airlines due to wether issue, our seats booked with no checked in luggage when I already payed for. We end up to pay 90 euro per suitcase.
Booked with Kayak… Economy Class it said. I had filtered for 1 checked bag. Get to boarding and it says I have Economy Light w/ no checked bags. $136 each way for baggage now. Do not use smartfares.com. Very misleading and a terrible start to this trip.
Overall good. I was surprised how easy it was to get from plain to plain in such a short time. Food choices were not so great and quite expensive. Entertainment was ok. Flights were smooth.
Our three ski bags did not arrive and are still not delivered, one full day later. With one ski bag not traceable at all. I would not fly Iceland Air again.
Horrible. The flight was delayed by over 3 hours but updates were barely provided. Boarding started 3 hours late then stopped because their system crashed. So now, passengers were standing for 15 minutes in the open waiting to get boarding passes scanned and get on a bus. Duty-free closed around 4-4:30. Only 1 food outlet was open and it was super slow and busy since it was serving passengers from multiple flights. So a number of passengers couldn't buy meals at the terminal. Since the flight was delayed by over 3 hours, we could have been offered snacks on-board. Nothing. The seats barely reclined. In-flight entertainment options were pitiful. Overall, a miserable experience. Never flying on Icelandair ever again. :(
Bad. Flights were late, by hours. No clear information was provided even until the delayed boarding time.
Again, lines for boarding are a problem in iceland. The flight itself was fine and very smooth. No complaints. We would definitely fly icelandair again.
take snacks and food. purchase options in flight are not great
Awful. The flight wasn't actually operated by Iberia, but by American Airlines. I was unable to get my boarding pass and as a result missed my connecting flight.
The seats were way too crowded. Just because I do not have the luxury of a suite, does not mean that I want to fly from Austin to London scrunched between two people and the seat in front of me in my face. Ridiculous. I should have flown with Turkish Airlines...
We travelled with Level, which is a subsidiary of Iberia. They mixed up all our seats, downgraded few from premium economy fo economy. The crew were not professional, they seem to be in a rush! Also some with an attitude
Paid for “extra room” selected seat. Wasn’t a benefit. Also was in aisle and was bumped almost every time attendants walked down aisle. Should have saved the assigned seat money and let them select.
Everything OK , except the plane left more than an hour late so I couldn’t participate in an excursion I had that morning in Brcelona
Flight from Madrid to Dakar had no onboard entertainment for a business class. Not even a single screen . That was disappointing. The WiFi only worked for the first 45 mins of the flight.
very good all round. staff, food, entertainment, punctuality all very good
The cabin crew were great very helpful and accommodating. We had a fellow passenger throw up next to us. The flight crew did an amazing job cleaning up and reseating us. We did question as to if he should have been let on the flight as his condition was likely self imposed.
online check-in was horrible and didn't work either way
Horrible. Paid for seats for my family. Iberia changed planes and never notified us that the seats we paid extra for did not even exist on the plane. We were randomly placed on the plane. Thankfully, we were seated together. Upon boarding, my youngest daughter was pulled from the line and they just arbitrarily changed her seat 7 rows back from the rest of the family. I had to wait at the gate while they tried to see us back together. One of the most uncomfortable small spaces on a plane I’ve ever experienced. When I called Iberia, they first told me that no mistake was made that the plane was never changed. Yet my receipt for my paid seats were for rows that did not even exist on this type of plane we were getting on. They said that they would reimburse my money and I would get an email, but I’ve never received any information or emails regarding a refund for the seats that I had paid extra for. Then when we arrived in Madrid, one of the pieces of luggage that we had checked in was damaged to the point that the handle that was stowed in to the luggage was broken off by the crew members handling the luggage. The crew on the plane was very nice, but as far as the rest of the experience, I would be very hesitant to ever use Iberia again.
The flight from Seattle was delayed, which made me miss my connection to Florence. I was re-booked NINE HOURS LATER!!! That’s basically a vacation day lost. British Airways needs to partner with other airlines when possible to get a more realistic travel time, if delays occur. I realize there aren’t many flights to Florence from London, so I would book differently were I to return. The actual flight from Seattle was very comfortable and the crew was great, no faults there. I enjoy British Airways, this was an anomaly.
The crew could not have been more helpful, my meal was excellent, I slept peacefully until right before landing, and the BA lounge was a godsend. The only negative I encountered was the coffee both on the plane and in the lounge. Not to my taste but that’s a personal preference.
I don’t understand why a reputable airline like BA would delegate their London flights to AA. Makes no sense to me, as most domestic carriers do such a poor job these days. Terminal 3 at LHR is a total dump
Cancelled flight minutes before boarding. Rescheduled flight was two days later
The flight attendants were EXTREMELY personable and appreciated the service, lights going off after dinner (probably the norm, but I haven’t flown evening overnight flights in a while). Thank you!
Business class seats were very dated on my plane. Very little storage, charging ports were not easily accessible, tv screen kept flopping away. Vegetarian food was disappointing: hardly any protein and severely under-seasoned. Crew was lovely.
The food was ok, but not great. They delayed boarding in Portland and did not enforce group boarding. But the crew was excellent, went above and beyond.
The food was pathetic. There wasn't much leg room and recline space for such a long flight. No tea/ coffee for a 2-3 hour connecting flight without purchasing! Really!?
Service was very good. Because I use a cane, I was allowed to use Priority Boarding. Biggest problem was extremely limited leg room in Economy class seats. For airplane food, it was alright.
Was late but that airport/storm fault. Flight was full but comfortable. Food quite nice. Unfortunate that I had a rather miserable attendant, others were much friendlier
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