Cheapest€63.27
- Korean Air KA992006:281h 21m07:49Toronto YYZChicago MDW
Door to door 4h 31mCO2 178.3 kgChanges 0Fixed, no changes
Traveling from Toronto to Chicago costs €63.27 at the cheapest and takes 4h 29m door to door at the fastest, across 1 mode and 13 operators. The route covers 725 km. Cheapest is by Flight, fastest is by Flight.
At a glance
- Distance
- 725 km
- Fastest
- 4h 29m
- Average
- 4h 34m
- Services per day
- 104
- Cheapest
- €63.27
- CO2 per passenger
- 178.3 kg
Every way to make this journey
Journey times below are door to door, so they include getting to the terminal and away from it at the other end. Fares are the cheapest we currently sell on September 29, 2026.
| Mode | Door to door | Moving | At the ends | From | CO2 | Per day |
|---|---|---|---|---|---|---|
| Flight | 4h 29m | 1h 19m | 3h 10m | €74.48 | 178.3 kg | 104 |
- 4h 29mFastest, by Flight
- €74.48Cheapest, by Flight
- 178.3 kgLowest CO2, by Flight
- 725 kmDistance traveled
The cheapest and the fastest on September 29, 2026
Two journeys we can sell today, with the service number each operator files them under.
Fastest€76.25
- ExpressJet EJ350018:381h 19m19:57Toronto YTZChicago ORD
Door to door 4h 29mCO2 178.3 kgChanges 0Fixed, no changes
Today's real departures
Live from the operators' own published timetables, through the open transit feeds they publish. Times and services are real. Fares are modeled until our booking connectors are live.
No live timetable for this trip yet.
Live from the operators' own published timetables, through the open transit feeds they publish. Times and services are real. Fares are modeled until our booking connectors are live.
Prices over the next three weeks
Live from our own engine, refreshed on every request. The cheapest days for each way of traveling are marked.
| Cheapest fare by mode and day for Toronto to Chicago | FriSep 11 | SatSep 12 | SunSep 13 | MonSep 14 | TueSep 15 | WedSep 16 | ThuSep 17 | FriSep 18 | SatSep 19 | SunSep 20 | MonSep 21 | TueSep 22 | WedSep 23 | ThuSep 24 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Flight | €156.49 | €137.61 | €128.17 | €92.18 | €90.41 | €96.31 | €120.50 | €91.00 | €93.36 | €86.87 | €75.66 | €74.48 | €78.61 | €96.90 |
Cheapest day: 2026-09-29 · €63.27
That is the traveling done. What happens after you walk out into Chicago is not something we sell.
Looking for somewhere to stay in Chicago?
The search opens on Chicago with your nights already filled in, so it is one step to a real price.
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When to book Toronto to Chicago
The same search run across the whole booking window, so the shape of the curve is visible rather than described.
- €64.4590 days
- €50.2960 days
- €60.3245 days
- €64.4530 days
- €76.8421 days
- €96.9014 days
- €120.507 days
- €128.173 days
- €156.491 days
- Cheapest lead time
- Fares bottom out around 60 days ahead, at €50.29.
- How much it moves
- The gap between the cheapest and most expensive lead time is 211 percent. The most expensive point is €156.49, 1 days out.
- What that means
- Today sits inside the cheap window, which closes about 60 days before departure. Waiting from here has usually cost money on this corridor rather than saved it.
Book now Fares on this route are lowest around 60 days ahead. You are inside that window.
Which departure day costs least
Median cheapest fare for each weekday, taken across the next three weeks of real prices.
- €86.87Sun
- €75.66Mon
- €74.48Tue
- €78.61Wed
- €96.90Thu
- €91.00Fri
- €93.36Sat
How the fare moves month by month
The same journey priced on the fifteenth of each of the next six months.
- €90.41Sep
- €67.40Oct
- €60.32Nov
- €60.91Dec
- €59.14Jan
- €51.47Feb
The route
What the journey actually looks like
Direct or connecting, how far the route really runs, and what happens when a connection is missed.
- How far it really runs
- The route covers 725 km against 704 km in a straight line, a detour of 3 percent. Track and road geometry account for the difference.
- First and last departure
- The first service of the day leaves Toronto at 06:01 and the last at 20:53, across 104 departures. The return direction keeps its own timetable, so the times back are not these times reversed.
Where you leave from and where you arrive
The stations, airports and ports each mode on this corridor actually uses.
Toronto
Rail
- Toronto Union Station
- North Toronto station
- Toronto Union Station (1858)
Bus
- Toronto Union Station Bus Terminal
- University of Toronto Scarborough
Air
- YYZ
- YTZ
Ferry
- Yonge
- Portland
Chicago
Rail
- Chicago Union Station
- Chicago Ridge
- Chicago station
Bus
- Chicago Union Station
- Chicago & Austin Terminal
Air
- ORD
- MDW
Ferry
- Chicago Avenue
- Chicago Riverwalk
Who runs this route
Speed, flexibility and what is on board. Nothing here is a rating, because we have not earned one.
| Operator | From | Fastest |
|---|---|---|
 Air Canada | €67.40 | 4h 30m |
 Air Canada Jazz | €66.81 | 4h 29m |
 Air Wisconsin | €65.04 | 4h 30m |
 American Airlines | €65.04 | 4h 29m |
 American Eagle Airlines | €64.45 | 4h 29m |
 Cathay Pacific | €66.22 | 4h 29m |
 EVA Air | €63.27 | 4h 30m |
 ExpressJet | €66.22 | 4h 29m |
 Korean Air | €63.27 | 4h 29m |
 Porter Airlines | €63.27 | 4h 30m |
 Republic Airways | €68.58 | 4h 30m |
 SkyWest | €64.45 | 4h 29m |
| United Airlines | €63.86 | 4h 29m |
What the fare is made of
Every part of the total, so the number at checkout is the number here.
| Part | Amount | Share |
|---|---|---|
| Operator fare | €46.00 | 73% |
| Taxes | €8.28 | 13% |
| Supplier fees | €7.00 | 11% |
| Our service fee | €1.99 | 3% |
| Total you pay | €63.27 | 100% |
A day in Chicago hauling a suitcase is a shorter day than it needs to be. We do not store bags.
Baggage storage near Chicago Union Station
Most of the points near Chicago Union Station open before the first train and close after the last one.
Check Chicago on StasherOr try Bounce
Partner links. We do not run these networks. We earn a commission on a booking, and the price is the same as going direct.
Questions about Toronto to Chicago
The questions people actually ask about this trip, answered from the same prices and times the page above is built on rather than written once and left to go stale.
How long does it take to get from Toronto to Chicago?
The fastest journey from Toronto to Chicago takes 4h 29m door to door, of which 1h 19m is spent moving, on the Flight. Most services take around 4h 34m, because that average includes slower stopping services and journeys with a connection. Times include reaching the terminal and leaving it at the far end.
How much does it cost to travel from Toronto to Chicago?
The cheapest fare from Toronto to Chicago is €63.27, checked on September 29, 2026. A typical fare across the next three weeks is €103.98. Both figures are the total for one passenger, including taxes, supplier fees and our service fee, so nothing is added at checkout.
What is the cheapest way to get from Toronto to Chicago?
The cheapest way from Toronto to Chicago is by Flight, at €74.48 for one passenger on September 29, 2026. That journey takes 4h 29m door to door. Cheaper is rarely faster on this corridor, and the comparison table on this page shows what each mode costs against what it saves.
When should I book Toronto to Chicago?
Fares from Toronto to Chicago bottom out around 60 days before departure, at €50.29. Across the whole booking window the gap between the cheapest and the most expensive lead time is 211 percent, measured on September 29, 2026. Booking inside the last week has consistently cost more on this corridor.
Which day of the week is cheapest for Toronto to Chicago?
Tuesday is the cheapest day to depart from Toronto to Chicago, at €74.48. That is the median of 21 priced departure days across the next three weeks, checked on September 29, 2026. Shifting a departure by one day is usually worth more than shifting the booking by one week.
Which month is cheapest for Toronto to Chicago?
February is the cheapest of the next 6 months to travel from Toronto to Chicago, at €51.47 for one passenger. Each month is priced on its fifteenth, so the comparison is like for like rather than a mix of weekends and midweek departures.
Who runs service from Toronto to Chicago?
13 operators sell services from Toronto to Chicago across 1 modes: Air Canada, Air Canada Jazz, Air Wisconsin, American Airlines, American Eagle Airlines, Cathay Pacific. Journey times, fares and fare conditions differ between them, and the operator table on this page compares all of them on speed, flexibility and what is provided on board.
Is there a direct service from Toronto to Chicago?
Every service we sell from Toronto to Chicago is direct, with around 104 departures a day and a fastest journey of 4h 29m door to door. No connection is needed, so there is no missed connection risk to plan around on this corridor.
Which station or terminal do services from Toronto to Chicago use?
Services from Toronto to Chicago by Flight leave from Toronto YTZ and arrive at Chicago ORD. Allow about 3h 10m in total for reaching the departure terminal and leaving the arrival one, which is already included in every door to door time on this page.
Can I change or refund a ticket from Toronto to Chicago?
0 of the 13 operators we sell from Toronto to Chicago allow a change or a refund. A change on a changeable fare costs €5.00. The operator table on this page names which is which, and the condition is shown again before you pay.
Where these numbers come from
Observed service A carrier record shows this named operator serving this named pair, and we carry that through unchanged.
Schedules, seat counts and fares are generated by our own model until the supplier contracts are signed. Places, coordinates, operators, which operator serves which pair, and every distance are real. We would rather say that on every page than let a modeled number pass for a filed one.
Defined in full at Door to door, Fares, The booking window, Carbon, Distances
- On this page
- Every figure above was computed for Toronto to Chicago on September 10, 2026: 725 km of route against 704 km in a straight line, 104 services a day, 13 operators, a cheapest fare of €63.27, and 4h 29m door to door on the fastest mode. The return direction is computed separately and its numbers are not these numbers.
The flight is the simple part. What you do once you are in Chicago is somebody else's catalog.
Anything to book in Chicago before you go?
Timed entry, guided walks and half-day trips out of Chicago, with free cancellation on most of it.
See Chicago on GetYourGuideOr browse Viator
Partner links. We do not sell tours or tickets. We earn a commission on a booking, and it never changes the price.
Other ways to make this journey
Arriving in Chicago
Leaving Chicago
- 266Places you can leave for
- 40Countries
- 77Operators
Plan a trip from here
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