Rome2Rio

How to get fromMaple Leaf to Chicagoby car, plane, taxi, bus, train or bus (Flixbus, Greyhound)

Find Transport to Chicago

See all options

There are 12 ways to get from Maple Leaf to Chicago by car, plane, taxi, bus, train, or bus (Flixbus, Greyhound)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Drive to Portland, fly to Chicago Midway International Airport

    best
    1. Drive from Maple Leaf to Portland-Airport-PWMcar
    2. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)planePWM - MDW
    7h 31m
    $149–608

  2. Drive to Bangor, fly to Chicago O'Hare International Airport

    cheapest
    1. Drive from Maple Leaf to Bangor-Airport-BGRcar
    2. Fly from Bangor (BGR) to Chicago O'Hare International Airport (ORD)planeBGR - ORD
    7h 58m
    $117–433

  3. Taxi, bus, train

    1. Take the taxi from Maple Leaf to Quebec - Coaticook Gorge Parktaxi
    2. Take the bus from Quebec - Coaticook Gorge Park to Montreal Tourist Information Center - 1255 Rue Peelbus
    3. Take the train from Montréal to Toronto Union Stationtrain
    4. Take the train from Toronto Union Station to Windsortrain
    5. Take the train from Detroit to Chicago Union Stationtrain
    20h 57m
    $262–491

  4. Bus

    1. Take the bus from Sherbrooke / Terminus to Montréal - Gare d'autocarsbus
    2. Take the bus from Montréal to Ottawabus
    3. Take the bus from Ottawa to Detroit Bus Stationbus
    4. Take the bus from Detroit Bus Station to Chicago Bus Stationbus
    27h 55m
    $244–463

  5. Drive 951.5 mi

    1. Drive from Maple Leaf to Chicagocar951.5 mi
    16h 29m
    $218–315

  6. Drive to Portland, fly to Chicago O'Hare International Airport

    1. Drive from Maple Leaf to Portland-Airport-PWMcar
    2. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)planePWM - ORD
    8h 12m
    $119–478

  7. Taxi, bus to Montréal–Pierre Elliott Trudeau International Airport, fly to Chicago O'Hare International Airport

    1. Take the taxi from Maple Leaf to Quebec - Coaticook Gorge Parktaxi
    2. Take the bus from Quebec - Coaticook Gorge Park to Montreal Tourist Information Center - 1255 Rue Peelbus
    3. Fly from Montréal–Pierre Elliott Trudeau International Airport (YUL) to Chicago O'Hare International Airport (ORD)planeYUL - ORD
    9h 12m
    $336–806

  8. Bus, train to Québec City Jean Lesage International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Sherbrooke to Drummondvillebus
    2. Take the train from Drummondville to Sainte-Foytrain
    3. Fly from Québec City Jean Lesage International Airport (YQB) to Chicago O'Hare International Airport (ORD)planeYQB - ORD
    11h 19m
    $386–1,056

  9. Drive, bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Drive from Maple Leaf to Berlincar
    2. Take the bus from Berlin to Concord, NHbus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)planeMHT - MDW
    11h 44m
    $155–654

  10. Bus, bus to Burlington International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Sherbrooke / Terminus to Montréal - Gare d'autocarsbus
    2. Take the bus from Montreal to Burlington Downtown Transit Ctrbus
    3. Fly from Burlington International Airport (BTV) to Chicago O'Hare International Airport (ORD)planeBTV - ORD
    12h 37m
    $217–634

  11. Bus, train via Albany

    1. Take the bus from Sherbrooke / Terminus to Longueuilbus
    2. Take the bus from Longueuil to Albany - Rensselaerbus
    3. Take the train from Albany-Rensselaer Amtrak Station to Chicago Union Stationtrain
    26h 22m
    $289–548

  12. Bus, train

    1. Take the bus from Sherbrooke / Terminus to Montréal - Gare d'autocarsbus
    2. Take the train from Montreal Central Station to Schenectadytrain
    3. Take the train from Schenectady to Chicago Union Stationtrain
    28h 13m
    $217–421

Portland (PWM) to Chicago Midway International Airport (MDW) flights

Calendar17Weekly Planes
Duration5h 11mAverage Duration
Ticket$111Cheapest Price
See schedules

Questions & Answers

What companies run services between Maple Leaf, QC, Canada and Chicago, IL, USA?

You can take a vehicle from Maple Leaf to Chicago Bus Station via Sherbrooke / Terminus, Montréal - Gare d'autocars, Montréal, Ottawa, and Detroit Bus Station in around 27h 55m.

Airlines
Train operators
Bus operators
Other operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Where to next?

Trips from Maple Leaf

Trips to Chicago

Popular routes