One passenger pays $65.89, every fee included. Services cover 694 km and are run by 2 operators across 1 mode.
What one seat costs
Every operator we hold on this corridor starts at $65.89, so there is no spread to show.
Typical fares · Priced for October 26, 2026
$65.89
- 163%Moves across the booking window
163%Departure times on this route
Departure times on this route12Go lists the departures it sells between Oakville and Chicago.
Partner link. The seller pays us a commission when a booking completes, and it never changes what you pay.
Fares by date
What this journey usually costs, by departure date. It shows which days run dearer.
Typical fares
- about $163.56Wed7
- about $183.58Thu8
- about $138.69Fri9
- about $112.61Sat10
- about $128.38Sun11
- about $118.06Mon12
- about $95.61Tue13
- about $98.65Wed14
- about $120.49Thu15
- about $92.58Fri16
- about $104.11Sat17
- about $96.83Sun18
- about $87.73Mon19
- about $73.17Tue20
- about $81.05Wed21
- about $99.26Thu22
- about $76.20Fri23
- about $82.88Sat24
- about $94.40Sun25
- about $65.89Mon26
- about $79.84Tue27
Based on what this route has cost recently. The live fare is confirmed when you book.
The train gets you into Chicago. These two partners take it from there, and the bed is theirs to book.
A room in Chicago for the night the train gets in
Sort by distance from Chicago Union Station and you can see which places are ten minutes on foot and which are not.
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When to book Oakville to Chicago
The same search run across the whole booking window, so the shape of the curve is visible rather than described.
- $62.8690 days
- $95.6160 days
- $62.2545 days
- $80.4530 days
- $79.8421 days
- $73.1714 days
- $95.617 days
- $138.693 days
- $163.561 days
- Cheapest lead time
- Fares bottom out around 45 days ahead, at $62.25.
- How much it moves
- The gap between the cheapest and most expensive lead time is 163 percent. The most expensive point is $163.56, 1 days out.
- What that means
- Today sits inside the cheap window, which closes about 45 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 45 days ahead. You are inside that window.
This corridor, specifically
Facts that apply to Oakville to Chicago and to no other route on the site.
Clocks
1 hours behind on arrival. You land earlier than the journey suggests.
The shape of it
694 km
675 km as the crow flies, 3% further by the route services take. The bearing runs west.
Who lives at each end
213,759 → 2,664,452
Population at the departure city and at the arrival city, which is usually what decides how often anything runs.
The route
What the journey looks like
Direct or connecting, how far the route really runs, and what happens when a connection is missed.
- Direct or connecting
- 0% of the services we sell on this corridor run through without a change. The remaining 100% involve one connection.
- How far it really runs
- The route covers 694 km against 675 km in a straight line, a detour of 3 percent. Track and road geometry account for the difference.
- Where the change is
- Connections are made at London. The gap between arriving and leaving is 76 minutes, of which about 14 is walking.
- If the connection is missed
- The tightest connection we sell here has a 13 percent chance of not being made on the timetable alone. Part of this journey is a self transfer between separate tickets, so leave more time than the minimum and expect to check in again.
Who runs this route
The train gets in hours before any room is ready. Holding a bag is not what we sell.
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
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Questions about Oakville 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 Oakville to Chicago?
Oakville to Chicago covers 694 km. Each operator's own departure and arrival times for the date you pick are in the search at the top of this page, beside the total price.
How much does it cost to travel from Oakville to Chicago?
The cheapest fare from Oakville to Chicago is $65.89, as of October 6, 2026. A typical fare across the next three weeks is $96.83. 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 Oakville to Chicago?
The cheapest way from Oakville to Chicago is by train, at $65.89 for one passenger on October 26, 2026. The comparison table on this page shows what each mode costs side by side.
When should I book Oakville to Chicago?
Fares from Oakville to Chicago bottom out around 45 days before departure, at $62.25. Across the whole booking window the gap between the cheapest and the most expensive lead time is 163 percent, measured on October 6, 2026. Booking inside the last week has consistently cost more on this corridor.
Which day of the week is cheapest for Oakville to Chicago?
Tuesday is the cheapest day to depart from Oakville to Chicago, at $79.84. That is the median of 21 priced departure days across the next three weeks, as of October 6, 2026. Shifting a departure by one day is usually worth more than shifting the booking by one week.
Which month is cheapest for Oakville to Chicago?
February is the cheapest of the next 6 months to travel from Oakville to Chicago, at $51.94 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 Oakville to Chicago?
2 operators sell services from Oakville to Chicago across 1 mode: SkyWest, VIA Rail Canada. 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 Oakville to Chicago?
0 percent of the services we sell from Oakville to Chicago are direct. The rest connect at London, with about 76 minutes between the two services. Both legs are sold on one booking, so a missed connection is rebooked at no charge.
Which station or terminal do services from Oakville to Chicago use?
Services from Oakville to Chicago by train leave from Oakville GO Station and arrive at Chicago O'Hare International Airport ORD. Allow about 1h 57m 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 Oakville to Chicago?
1 of the 2 operators we sell from Oakville to Chicago allow a change or a refund. A change on a changeable fare costs $5.51. The operator table on this page names which is which, and the condition is shown again before you pay.
Where these numbers come from
Places, coordinates, operators, which operator serves which pair, and every distance on this page are real and come from open data. Where a corridor has a filed timetable the departure times are real too, and ferry fares are the prices the operators publish themselves.
Observed service A carrier record names this operator on this pair, carried through unchanged.
Prices come from the supplier wherever we hold a live quote. Elsewhere we show an indicative price built from the real distance, the real operator and a fare curve over lead time, day of the week and season. Those are labeled Estimated fare and cannot be booked.
Defined in full at Door to door, Fares, The booking window, Carbon, Distances
Being on the water gives Chicago a set of days out that do not start at a station.
Day trips out of Chicago and across United States
Day trips that leave Chicago in the morning and cover a good part of United States by evening.
See Chicago on GetYourGuideOr browse Viator
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The two ends, compared
Oakville reaches 19 places in 3 countries on services we hold, over distances from 27 to 5,746 km. Chicago reaches 98 places in 21 countries, from 59 to 15,696 km.
Other ways to make this journey
Leaving Oakville
- 19Places you can leave for
- 3Countries
- 3Operators
3
3Arriving in Chicago
Leaving Chicago
- 98Places you can leave for
- 21Countries
- 48Operators