Chicago to London: Cheapest Flight Options 2023

Flying from Chicago to London doesn’t have to drain your wallet. Whether you’re planning a business trip, a cultural adventure, or visiting family across the Atlantic, finding affordable flights from Chicago to London requires strategy, timing, and knowledge of the best booking practices. This comprehensive guide will walk you through every option available to budget-conscious travelers in 2023, from traditional carriers to budget airlines, peak season considerations, and insider tips that could save you hundreds of dollars on your transatlantic journey.

Chicago’s two major airports—O’Hare International Airport (ORD) and Midway International Airport (MDW)—offer numerous daily connections to London’s primary hubs: Heathrow (LHR), Gatwick (LGW), Stansted (STN), and Luton (LUW). The competition among airlines on this route is fierce, which works in your favor as a savvy traveler. Understanding the nuances of each airline’s pricing strategy, seasonal variations, and booking windows can mean the difference between a $400 ticket and a $900 ticket for the same route.

Major Airlines Operating Chicago to London Routes

Several established carriers dominate the Chicago-London corridor, each with distinct pricing models and service offerings. United Airlines operates the most frequent direct flights from O’Hare to both Heathrow and Gatwick, typically offering multiple daily departures. While United isn’t always the cheapest option, their frequent scheduling provides flexibility for date changes without rebooking fees. British Airways maintains a strong presence on this route with competitive pricing, especially when booked well in advance through their website.

American Airlines offers competitive fares through their partnership with British Airways, and their frequent flyer program integration can provide value for loyalty program members. Best airlines for long flights often include these legacy carriers for their comfort and service consistency, though budget isn’t always their primary advantage. Delta Air Lines provides daily service from Chicago, often with competitive pricing during off-peak seasons. Norse Atlantic Airways entered the market in 2023 as a true low-cost transatlantic carrier, offering remarkably cheap base fares, though additional fees for baggage, seat selection, and other services can add up quickly.

Air Canada and WestJet occasionally offer connecting flights through Toronto that can compete on price, particularly for flexible travelers willing to add 3-5 hours to their journey. These options deserve consideration when comparing total trip costs rather than just direct flight prices. The key is checking multiple carriers simultaneously rather than assuming direct flights are always cheaper than one-stop alternatives.

Budget Carrier Options and Hidden Fees

The emergence of budget transatlantic carriers has fundamentally changed pricing dynamics on the Chicago-London route. Norse Atlantic Airways offers base fares starting as low as $99-$199 one-way, making them an attractive option for price-sensitive travelers. However, their ultra-low-cost model means that checked baggage (typically $85-$110 each direction), seat selection ($15-$40), and meal services carry additional charges. A seemingly cheap $149 ticket can become $350+ once you factor in necessary add-ons.

Before committing to budget carriers, calculate your total trip cost including all anticipated fees. If you’re packing light with only a carry-on bag and can forgo seat selection preferences, budget airlines represent genuine savings. How to book refundable airline tickets becomes especially important with budget carriers, as their change and cancellation policies are significantly more restrictive than traditional airlines. Many budget carriers offer non-refundable fares exclusively, meaning you’ll lose your entire ticket cost if your plans change.

Frontier Airlines occasionally offers Chicago-London flights through partnerships, though these typically involve connections. Always read the fine print regarding baggage allowances, seat selection policies, and cancellation terms. What appears as the cheapest option might become expensive once hidden fees are revealed.

Seasonal Pricing and Best Times to Book

Chicago-London airfares follow predictable seasonal patterns. Summer months (June-August) represent peak season with prices typically 40-60% higher than winter. Fall shoulder season (September-October) offers a sweet spot with pleasant weather and moderate prices. Winter months (November-February, excluding December 20-January 5) feature the lowest fares, though weather and shorter daylight hours are trade-offs. Spring (March-May) gradually increases in price as summer approaches.

The best times to book airline tickets for transatlantic flights typically occurs 2-3 months in advance. For summer travel, booking by late March or early April usually captures optimal pricing. For winter getaways, booking in August or September provides the best rates. Booking too far in advance (6+ months) or too close to departure (within 2-3 weeks) generally results in higher prices, though last-minute deals occasionally emerge.

Tuesday and Wednesday departures from Chicago consistently offer cheaper fares than Friday-Sunday travel. Tuesday-Thursday flights in London also tend to be cheaper than weekend arrivals. If your schedule permits, shifting your travel by just one or two days can yield 15-30% savings. Mid-week flights are less popular with leisure travelers, creating pricing opportunities for flexible travelers.

Using Flight Comparison Tools Effectively

Modern flight comparison tools are essential for finding the cheapest options, but using them effectively requires strategy. Google Flights excels at price tracking and flexible date searches, allowing you to view calendar pricing across an entire month. Set up price alerts for your desired route—Google will email you when fares drop below your specified threshold. The “Flexible Dates” feature shows price differences across multiple dates simultaneously, making it easy to identify the cheapest travel windows.

Kayak and Skyscanner aggregate fares from hundreds of airlines and booking sites, sometimes revealing options that other tools miss. Skyscanner’s “Everywhere” feature is particularly useful for exploring alternative London airports; sometimes flying into Stansted or Luton instead of Heathrow or Gatwick saves $50-$150. Kayak’s “Hacker Fares” feature identifies when booking outbound and return flights separately on different airlines results in lower total costs than round-trip bookings.

ITA Matrix by Google provides transparent pricing information and allows advanced filtering by departure times, airline preferences, and route preferences. Momondo specializes in finding hidden deals and occasionally displays fares unavailable on other platforms. However, directly booking through airline websites sometimes offers loyalty program discounts or exclusive fares not available through third-party booking sites.

Always compare prices across multiple tools before booking. Price discrepancies between platforms can be substantial. Clearing your browser cookies and using incognito/private browsing mode prevents flight comparison sites from tracking your searches and potentially inflating prices based on repeated queries.

Booking Strategies to Maximize Savings

Strategic booking decisions can substantially reduce your Chicago-London flight costs. Booking round-trip flights is typically cheaper than separate one-way tickets, though occasionally booking outbound and return separately on different airlines (Kayak’s Hacker Fares) yields savings. Open-jaw tickets—flying into one London airport and out of another—sometimes cost less than standard round-trip options and provide logistical advantages.

Consider booking from Chicago’s Midway Airport (MDW) instead of O’Hare (ORD). While Midway has fewer direct flights to London, connecting options through various hubs often cost significantly less. The time investment of a connection might be worthwhile if you’re saving $100-$200 on airfare. Similarly, flying to alternative London airports (Gatwick, Stansted, Luton) rather than Heathrow can reduce fares by 20-40%, though consider ground transportation costs when comparing total trip expenses.

Incognito/private browsing mode prevents airline websites from tracking your searches and inflating prices based on your repeated queries. Clear your cookies between searches or use a VPN with a different IP address when comparing fares. Some travelers report that searching from different geographic locations yields different prices, though this practice’s legality varies by jurisdiction.

Booking flexibility is your greatest asset. Flexible travelers who can depart mid-week, during shoulder seasons, or adjust their travel dates by a few days will consistently find cheaper fares. If your schedule allows, booking round-trip flights with flexible return dates (returning within 10-21 days rather than exactly 7 days) often costs less per night abroad.

Alternative Routing and Connecting Flights

Direct flights from Chicago to London are convenient but not always cheapest. Exploring one-stop and two-stop itineraries frequently reveals significant savings. Common connecting hubs include Toronto (Air Canada), Boston (United), New York (American, United, Delta), and Washington DC (United). A flight with a 2-3 hour connection in Toronto might cost $150-$250 less than a direct flight, and the time investment of a connection is often worthwhile.

Transatlantic flights from secondary US cities sometimes cost less than Chicago flights. Driving to or flying to Indianapolis, Detroit, or St. Louis for a cheaper transatlantic connection might reduce total trip costs despite additional ground transportation. This strategy works particularly well for travelers in southern Illinois, Indiana, or Ohio. Use flight comparison tools to check fares from multiple nearby airports simultaneously.

Positioning flights—flying from Chicago to a major hub like New York or Boston on a separate, cheaper carrier before catching your transatlantic flight—occasionally result in overall savings. A $200 positioning flight plus a $400 transatlantic connection from a major hub might cost less than a $700 direct flight from Chicago. This strategy requires careful timing to ensure connections are feasible and comfortable.

Airline Loyalty Programs and Points

Frequent flyer programs add substantial value to Chicago-London flights, particularly for regular travelers. United Airlines MileagePlus members accumulate miles on direct Chicago-London flights, and award flights to London typically require 60,000-80,000 miles in economy. If you fly frequently within the US, these miles accumulate quickly, effectively making transatlantic flights free or heavily discounted.

British Airways Executive Club members earn Avios points on transatlantic flights, with award availability starting at 40,000 Avios for economy flights to London. American Airlines AAdvantage and Delta SkyMiles programs similarly reward transatlantic travel. If you have existing balances in any loyalty program, redeeming miles for Chicago-London flights often provides better value than paid fares.

Airline credit cards offer sign-up bonuses (typically 50,000-75,000 points) that can cover or nearly cover a transatlantic flight. Annual fees ($95-$550) are often waived for first-year cardholders, making these cards an excellent value for planned international travel. However, only pursue credit card strategies if you can pay off balances immediately, as interest charges eliminate any savings.

Travel Insurance and Fare Protection

While not directly reducing flight costs, travel insurance protection safeguards your investment. Trip cancellation insurance reimburses your entire flight cost if covered events force you to cancel, protecting your savings on discounted non-refundable fares. Comprehensive travel insurance typically costs $100-$300 for a transatlantic flight and covers medical emergencies, lost luggage, and flight disruptions.

Certain credit cards include travel insurance benefits for cardholders, potentially eliminating the need for separate policies. Check your credit card’s benefits guide before purchasing standalone insurance. Budget airlines’ restrictive refund policies make travel insurance particularly valuable when booking ultra-low-cost fares.

Some travel insurance policies include “cancel for any reason” coverage (at premium rates) that reimburses flights even if you simply change your mind. For budget-conscious travelers booking non-refundable fares, this protection provides valuable peace of mind and can be worth the additional cost.

Monitor airline policies regarding schedule changes and rebooking. Most airlines allow free rebooking on alternate flights if they change your schedule, and some offer automatic rebooking on better flights at no charge. Understanding these policies helps you navigate disruptions without losing your investment.

FAQ

What is the cheapest month to fly from Chicago to London?

January through March (excluding holiday periods) typically offers the cheapest fares, with February usually being the absolute cheapest month. November also provides excellent pricing as summer demand ends. Avoid June through August peak season unless flexibility is impossible.

How far in advance should I book Chicago to London flights?

For optimal pricing, book 2-3 months in advance. For summer travel, book by late March or early April. For winter travel, book in August or September. Booking too far in advance (6+ months) or too close to departure (within 2-3 weeks) generally results in higher prices.

Are budget airlines really cheaper when you include all fees?

Budget airlines like Norse Atlantic offer cheap base fares but add fees for baggage, seat selection, and other services. If you’re packing light with only a carry-on, they’re genuinely cheaper. If you need checked baggage, the savings diminish significantly. Always calculate total trip costs including all anticipated fees.

Should I book a direct flight or a connecting flight?

Connecting flights frequently cost $100-$300 less than direct flights. If you’re flexible with travel time and comfortable with connections, one-stop flights offer substantial savings. The time investment is often worthwhile for significant price reductions.

Can I find cheaper flights by flying into a different London airport?

Yes, flying into Gatwick, Stansted, or Luton instead of Heathrow often costs 20-40% less. However, consider ground transportation costs to central London when comparing total trip expenses. Stansted and Luton are farther from central London, adding $15-$30 to ground transportation costs.

Do airline loyalty programs provide value for Chicago-London flights?

Yes, if you have existing mile balances. Award flights typically require 60,000-80,000 miles in economy. If you fly domestically frequently, these miles accumulate quickly, making transatlantic flights free or heavily discounted. Airline credit card sign-up bonuses can also cover flight costs.

What days of the week are cheapest for Chicago-London flights?

Tuesday and Wednesday departures from Chicago offer cheaper fares than Friday-Sunday travel. Departing on off-peak days can save 15-30% compared to weekend flights. If your schedule permits flexibility, adjust your travel dates to mid-week departures.

Is travel insurance worth purchasing for budget airline tickets?

Yes, especially for budget airlines with restrictive refund policies. Travel insurance reimburses your entire flight cost if covered events force cancellation, protecting your savings on non-refundable fares. Comprehensive policies typically cost $100-$300 for transatlantic flights.

Can I save money by booking outbound and return flights separately?

Occasionally, but rarely. Round-trip bookings are usually cheaper than separate one-way tickets. However, Kayak’s Hacker Fares feature sometimes identifies situations where booking each leg separately on different airlines costs less. Always compare round-trip and separate one-way pricing.

What flight comparison tools are most reliable for Chicago-London routes?

Google Flights excels at price tracking and flexible date searches. Skyscanner is excellent for exploring alternative airports. Kayak specializes in revealing hidden deals. Check prices across multiple platforms before booking, as discrepancies can be substantial.