30+ airlines to Chicago (ORD)BNPL at checkoutInstant e-ticket deliveryFlag of United States

Flights to Chicago: Search, Compare and Pay in Installments

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Scenic view of Chicago, US
Where from?Add a city
Where to?ChicagoAll airports
WhenOut – Back
Who1, Economy

Over a million travelers a year
find flights on Laters.com

BNPL at checkout

Pay for Your Chicago Flight in Instalments

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.

Chicago – BNPL providers

Chicago on Laters.com: key facts

Airlines flying to Chicago
30+
Airport
ORD
From the Loop
27 km
Cheapest month to fly
January
Laters Destination Score
7.3 / 10
New York to Chicago, direct
2h 30m

Score based on Laters booking data and editorial review.

40+ProvidersFly now pay later with 40+ providersSplit the cost, pay in 4, or spread larger fares, with 40+ providers in a single checkout.See all ways to pay
3 simple steps

How to Book Chicago Flights with BNPL

From search to e-ticket in under three minutes.

  1. Search Chicago flights

    Enter your origin city, select Chicago (ORD) as destination, pick your travel dates and passenger count, and compare airlines side by side.

  2. Choose BNPL

    Select your pay-later provider on the payment screen and pick your instalment plan. Instant approval — no hard credit check for most plans.

  3. Fly now, pay later

    Your Chicago e-ticket arrives in your inbox immediately. Your BNPL provider manages payments automatically. Pack your bags.

Proprietary research

Laters.com Destination Score for Chicago

Scored by our editorial team using booking data, traveller feedback, and independent research. No destination pays to be rated.

Chicago – destination score
Cyan cartoon hand making a peace sign with black outline sticker style illustration

What is the Laters Destination Score?

Chicago · ORD · United States, scored out of 10 on 6 measures.

  1. 1Value for Money
  2. 2Flight Frequency
  3. 3BNPL Availability
  4. 4Airport Experience
  5. 5Visa Ease
  6. 6Destination Appeal

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.

Flying 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.

What works well

  • World-class food
  • Huge flight choice
  • Great BNPL coverage

What to watch

  • Book early Dec-Jan
  • O'Hare can delay
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.
Editorial snapshotLaters.com editorial team
Price calendar

When to Book Flights to Chicago

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.

Chicago – when to book
MonthPrice BandDemandTravel note
JanuaryBudgetLowColdest month; polar vortex possible, but fares are lowest.
FebruaryBudgetLowValentine's weekend spikes city hotel rates slightly.
MarchMidMediumSt. Patrick's Day dyeing of the Chicago River draws crowds.
AprilMidMediumSpring arrives late; weather unpredictable but pleasant.
MayMidMediumCraft beer and food festivals begin; good value window.
JunePeakHighChicago Blues Festival draws large crowds to Grant Park.
JulyPeakHighLollapalooza and summer tourism push fares to annual highs.
AugustPeakHighBest weather; book 10+ weeks ahead for reasonable fares.
SeptemberMidHighAir and Water Show; shoulder season begins late month.
OctoberMidMediumFall foliage along the lakefront; pleasant temperatures.
NovemberPeakHighThanksgiving week is the single most expensive travel period.
DecemberPeakHighChristkindlmarket and holiday travel keep fares elevated.

Before you pick a month

Cheapest month
January — average fares around $89 one-way.
Peak season warning
July, Thanksgiving week, and late December: fares typically rise 50–70% above average. Book 10–14 weeks ahead.

Fares are estimates based on typical prices and may vary by date and availability.

Arrival guide

What to Know About Chicago Airport

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, so 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.

Chicago – airport guide
TransportCost (approx)Duration
CTA Blue Line (El train)USD 545 min to downtown Loop
Metered taxi / rideshareUSD 35–5530–60 min depending on traffic
GO Airport Express shuttleUSD 35–40 per person45–75 min to city hotels

Chicago Midway International Airport

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.

TransportCost (approx)Duration
CTA Orange Line (El train)USD 530 min to downtown Loop
Metered taxi / rideshareUSD 20–3520–40 min to the Loop
Pace busUSD 245–60 min to Midway CTA station

Check-in tips

  • Enrol in TSA PreCheck before flying, since O'Hare lines without it can add 40 minutes.
  • International arrivals at Terminal 5 should allow 90 minutes for customs and baggage claim.
  • Southwest at Midway boards by group number, not seat, so check in exactly 24 hours early.

Splitting the extras

  1. At Laters.com checkout you can split the cost of seat upgrades, extra baggage, and lounge access passes for O'Hare into instalments using Klarna, Afterpay, or Affirm, all confirmed instantly alongside your ticket.
Popular routes

Popular Flights to Chicago

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.

From North America

New YorktoChicago

American, United, Delta · 2h 30m · Direct

From

$37× 3

Pay in 3, on a $110 fare

Los AngelestoChicago

United, American, Delta · 4h 10m · Direct

From

$43× 3

Pay in 3, on a $130 fare

TorontotoChicago

Air Canada, United, American · 1h 40m · Direct

From

$50× 3

Pay in 3, on a $150 fare

Mexico CitytoChicago

Aeroméxico, United, American · 4h 00m · Direct

From

$73× 3

Pay in 3, on a $220 fare

MiamitoChicago

American, United · 3h 10m · Direct

From

$38× 3

Pay in 3, on a $115 fare

From Europe

LondontoChicago

United, British Airways, American · 9h 20m · Direct

From

$120× 4

Pay in 4, on a $480 fare

FrankfurttoChicago

Lufthansa, United · 9h 45m · Direct

From

$128× 4

Pay in 4, on a $510 fare

From East Asia

TokyotoChicago

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.

Explore more

Other Destinations Near Chicago

These destinations are popular with travellers who also searched for Chicago on Laters.com.

Fares are estimates based on typical prices and may vary by date and availability.

Rated 4.7 on Google

What Travellers Say

Real reviews from real customers who booked flights with Laters.com.

FAQ

Frequently Asked Questions about Flights to Chicago

Everything you need to know before booking your Chicago flight on Laters.

Which airlines fly direct to Chicago O'Hare (ORD)?

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.

What is the cheapest month to fly to Chicago?

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.

Can I pay for flights to Chicago in instalments on Laters.com?

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, with the instalment schedule beginning after booking. No changes are made to your booking confirmation regardless of which plan you choose.

Does using BNPL for flights affect my credit score?

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.

Do I need a visa to visit Chicago from the UK or Australia?

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, so 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.

How do I get from O'Hare Airport to downtown Chicago?

The CTA Blue Line train runs directly from O'Hare to the downtown Loop in about 45 minutes for a flat fare of $5, making it 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.

What is the best time of year to visit Chicago?

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.

How long is the flight to Chicago from London?

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.

When will I receive my e-ticket after booking on Laters.com?

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.

Is Chicago Midway (MDW) or O'Hare (ORD) better for my trip?

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, making it the better pick for Southwest Airlines domestic flights and for travellers staying outside the Loop. Check which airport your airline uses before booking.

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