New YorktoChicago
American, United, Delta · 2h 30m · Direct
From
$37× 3
Pay in 3, on a $110 fare
30+ airlines to Chicago (ORD)BNPL at checkoutInstant e-ticket delivery
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Klarna, Afterpay, and Affirm are all available at Laters.com checkout for flights to Chicago. Choose your plan, get approved in seconds, and your e-ticket lands in your inbox immediately. Split a Chicago fare into manageable instalments without touching your savings.
Book flights across 650+ airlines and pay later, your way. Split the cost, pay in 4, or spread larger fares, with 40+ providers in a single checkout.
Score based on Laters booking data and editorial review.
Klarna splits your Chicago fare into four equal payments, charged every two weeks — zero interest, no hidden fees. Approval takes seconds at checkout, and your booking is confirmed instantly. A solid choice whether you're flying from New York, London, or Sydney.
Available in the US, UK, Canada, Australia, and 20+ markets
Afterpay divides your fare into four fortnightly payments — the first is due at booking, the rest follow automatically. No interest charges apply as long as you pay on time. Popular with US-based travellers booking domestic connections into O'Hare.
Available in the US, Australia, New Zealand, Canada, UK
From search to e-ticket in under three minutes.
Enter your origin city, select Chicago (ORD) as destination, pick your travel dates and passenger count, and compare airlines side by side.
Select your pay-later provider on the payment screen and pick your instalment plan. Instant approval — no hard credit check for most plans.
Your Chicago e-ticket arrives in your inbox immediately. Your BNPL provider manages payments automatically. Pack your bags.
Scored by our editorial team using booking data, traveller feedback, and independent research. No destination pays to be rated.
Chicago · ORD · United States, scored out of 10 on 6 measures.
Every destination we sell flights to is scored on the same 6 measures, so you can compare Chicago with anywhere else before you choose where to go. Compare every destination →
Score based on Laters booking data and editorial review, 2026. No destination pays to be rated.
August and September are Chicago's sweet spot: warm lake breezes, the city's best outdoor festivals, and fares that haven't yet hit holiday-season peaks. January and February are the cheapest months to fly, but the wind chill off Lake Michigan is not a metaphor. Book 6–8 weeks ahead for the best domestic fares; 10–14 weeks for international routes.
| Month | Price Band | Demand | Travel note |
|---|---|---|---|
| January | Budget | Low | Coldest month; polar vortex possible, but fares are lowest. |
| February | Budget | Low | Valentine's weekend spikes city hotel rates slightly. |
| March | Mid | Medium | St. Patrick's Day dyeing of the Chicago River draws crowds. |
| April | Mid | Medium | Spring arrives late; weather unpredictable but pleasant. |
| May | Mid | Medium | Craft beer and food festivals begin; good value window. |
| June | Peak | High | Chicago Blues Festival draws large crowds to Grant Park. |
| July | Peak | High | Lollapalooza and summer tourism push fares to annual highs. |
| August | Peak | High | Best weather; book 10+ weeks ahead for reasonable fares. |
O'Hare International Airport, IATA ORD · 27 km from the Loop · 32 km from Navy Pier.
O'Hare is one of the world's busiest airports, with four passenger terminals handling everything from United's transatlantic hub to American's domestic network and international carriers from Lufthansa to Air China. Terminal 5 handles most international arrivals and has its own customs hall — factor in 45–75 minutes for immigration on busy days. The underground neon-lit walkway connecting Terminals 1, 2, and 3 is genuinely worth slowing down for.
| Transport | Cost (approx) | Duration |
|---|---|---|
| CTA Blue Line (El train) | USD 5 | 45 min to downtown Loop |
| Metered taxi / rideshare | USD 35–55 | 30–60 min depending on traffic |
| GO Airport Express shuttle | USD 35–40 per person | 45–75 min to city hotels |
Chicago Midway International Airport, IATA MDW · 13 km from the Loop · 10 km from Wicker Park.
Midway is Southwest Airlines' Chicago stronghold, handling the bulk of budget domestic traffic along with some Frontier and Spirit services. The terminal is compact and significantly easier to navigate than O'Hare, with shorter security lines on most days. No international customs hall here — all arrivals are domestic or pre-cleared.
| Transport | Cost (approx) | Duration |
|---|---|---|
| CTA Orange Line (El train) | USD 5 | 30 min to downtown Loop |
Make your Chicago trip work harder by splitting every extra at checkout.
Lock in a window seat for the approach over Lake Michigan's shoreline.
Chicago's winters demand coats; extra baggage allowance keeps your packing honest.
O'Hare weather delays are real — travel insurance covers cancellations and missed connections.
Bundle a Loop hotel with your fare and pay for both in instalments.
Pre-book a transfer from O'Hare to your hotel and skip the taxi queue entirely.
A US data SIM keeps Google Maps running on the CTA without roaming charges.
Chicago O'Hare is a true hub airport — travellers arrive from New York, Los Angeles, London, Toronto, and Tokyo, among dozens of other cities. Most major US metros have multiple daily direct options, while international routes tend to cluster around United's global network.
American, United, Delta · 2h 30m · Direct
From
$37× 3
Pay in 3, on a $110 fare
United, American, Delta · 4h 10m · Direct
From
$43× 3
Pay in 3, on a $130 fare
Air Canada, United, American · 1h 40m · Direct
From
$50× 3
Pay in 3, on a $150 fare
Chicago O'Hare is co-dominated by United and American Airlines, which together account for the majority of seats. Beyond the big two, a strong spread of international and budget carriers rounds out the options for every type of traveller.
O'Hare is United's largest hub; unmatched frequency on domestic routes and direct transatlantic and transpacific services.
Strong domestic network from O'Hare with direct routes to London, Tokyo, and major Latin American cities.
Competitive domestic fares from O'Hare and Midway, with solid connections via Atlanta and Detroit for international travellers.
Midway's dominant carrier; no seat fees, two free checked bags, and low domestic fares make it the budget-savvy pick.
Daily Frankfurt–Chicago O'Hare service with strong onward connections across Europe and business-class upgrade options.
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Space City with a serious barbecue habit.
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Art deco, ocean air, and late-night energy.
Fares are estimates based on typical prices and may vary by date and availability.
Everything you need to know before booking your Chicago flight on Laters.
United Airlines and American Airlines operate the most direct flights to O'Hare, with combined service from dozens of US cities and international destinations including London, Frankfurt, Tokyo, and Mexico City. British Airways, Lufthansa, ANA, and Air France also run nonstop transatlantic and transpacific routes. You can compare all direct and connecting options on Laters.com.
January and February are typically the cheapest months to fly to Chicago, with average one-way domestic fares sometimes dipping below $100. Demand is low due to cold weather, which works in a budget traveller's favour. Avoid Thanksgiving week, the Fourth of July period, and late December, when fares can rise 50–70% above the annual average.
Yes. Laters.com supports Klarna, Afterpay, Affirm, and Sezzle at checkout for Chicago flights. You choose your plan, get approved in seconds, and receive your e-ticket immediately — the instalment schedule begins after booking. No changes are made to your booking confirmation regardless of which plan you choose.
It depends on the provider. Klarna and Afterpay's standard pay-in-4 plans typically use a soft credit check that does not affect your credit score. Affirm's longer monthly plans may involve a hard inquiry. Always review the provider's terms before completing checkout.
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Singapore Travel Agent LicenceTA04059Flying to Chicago rewards the traveller who books early and stays flexible. Domestic fares from the East Coast are often under $120, while transatlantic routes from London or Frankfurt tend to be competitive in shoulder season. O'Hare suits frequent flyers who know its quirks; Midway is the smarter choice for budget carriers. Best suited to city-break enthusiasts, architecture obsessives, and anyone who takes food seriously.
January fares dip to $89, but that's Lake Michigan wind chill you're buying into, so weigh the saving against the scarf budget. O'Hare's Terminal 5 customs hall can eat 45 to 75 minutes on busy days, and anything under a 60-minute connection is a gamble not worth taking. The neon underground walkway between Terminals 1, 2, and 3 is the one part of the airport worth savouring rather than rushing. Klarna, Afterpay, Affirm, and Sezzle all clear at checkout with instant approval, which is more than can be said for O'Hare's timetable in July.
| September | Mid | High | Air and Water Show; shoulder season begins late month. |
|---|
| October | Mid | Medium | Fall foliage along the lakefront; pleasant temperatures. |
|---|
| November | Peak | High | Thanksgiving week is the single most expensive travel period. |
|---|
| December | Peak | High | Christkindlmarket and holiday travel keep fares elevated. |
|---|
Fares are estimates based on typical prices and may vary by date and availability.
| Metered taxi / rideshare | USD 20–35 | 20–40 min to the Loop |
|---|
| Pace bus | USD 2 | 45–60 min to Midway CTA station |
|---|
Aeroméxico, United, American · 4h 00m · Direct
From
$73× 3
Pay in 3, on a $220 fare
American, United, Spirit · 3h 10m · Direct
From
$38× 3
Pay in 3, on a $115 fare
United, British Airways, American · 9h 20m · Direct
From
$120× 4
Pay in 4, on a $480 fare
Lufthansa, United · 9h 45m · Direct
From
$128× 4
Pay in 4, on a $510 fare
ANA, United, Japan Airlines · 13h 30m · Direct
From
$180× 4
Pay in 4, on a $720 fare
Each figure leads with the instalment; the fare beside it is the whole fare that instalment splits. Fares are estimates based on typical prices and may vary by date and availability.
UK and Australian passport holders can enter the United States under the Visa Waiver Program using an ESTA (Electronic System for Travel Authorization), which costs $21 and is valid for two years or multiple trips. ESTA must be approved before departure — apply at least 72 hours in advance at the official US Customs and Border Protection website. Always check the latest requirements at travel.state.gov.
The CTA Blue Line train runs directly from O'Hare to the downtown Loop in about 45 minutes for a flat fare of $5 — it's the fastest and most reliable option outside of rush hour. Taxis and rideshare services (Uber, Lyft) cost roughly $35–55 depending on traffic and time of day. Shared shuttle services like GO Airport Express are available for around $35–40 per person.
August and September offer the best combination of weather and events: temperatures are warm (typically 22–28°C), the lakefront is at its most inviting, and the city's festival calendar is packed. Spring (April–May) is a good shoulder-season alternative with lower fares and fewer crowds. Winter visits are genuinely cold but rewarding if you come for the architecture, food scene, or the Christkindlmarket.
Direct flights from London Heathrow to Chicago O'Hare take approximately 9 hours 20 minutes westbound. The return journey (eastbound, with tailwinds) is typically 8 hours 30 minutes. British Airways and United Airlines both operate daily nonstop service on this route.
Your e-ticket is issued immediately upon booking confirmation, regardless of which payment method or BNPL plan you use. You'll receive a confirmation email with your booking reference and ticket within minutes of completing checkout.
O'Hare is the right choice for international arrivals and most major domestic routes, given its size and connectivity. Midway is smaller, easier to navigate, and closer to the South Side and Near West neighbourhoods — it's the better pick for Southwest Airlines domestic flights and for travellers staying outside the Loop. Check which airport your airline uses before booking.
Real reviews from real customers who booked flights with Laters.com.
