Stamford, CT, USA to Chicago, IL, USA from $42: 9 ways by bus, train, flight or car

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How to Get from Stamford to Chicago: Cheapest, Fastest and Best Way

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$42 by trainBest price

1183 kmDistance

5h 49m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Stamford to Chicago with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

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Traveling From Stamford to Chicago

Traveling from Stamford to Chicago reveals a journey from the quaint charm of Connecticut’s coastline to the vibrant, bustling atmosphere of the Windy City.

Best Neighbourhoods in Chicago

Chicago's neighborhoods offer diverse experiences, showcasing the city's vibrant culture.

Wicker Park

• Known for its artistic vibe and music scene.

• Plenty of trendy boutiques and dining options.

Lincoln Park

• Features beautiful parks and the Lincoln Park Zoo.

• Great for families and outdoor activities.

South Loop

• Home to museums like the Field Museum.

• Easy access to Lake Michigan's waterfront.

Best Times To Visit Chicago's Attractions

Timing your visits to Chicago's attractions can significantly enhance your experience.

The Art Institute of Chicago

Visit on weekdays, especially early mornings, to enjoy fewer crowds.

Millennium Park

Early mornings or weekday afternoons offer a quieter atmosphere for relaxation.

Navy Pier

Visit during non-peak hours on weekdays for a more enjoyable experience.

Chicago Weather: What to Expect Year-Round

Chicago experiences four distinct seasons, with cold winters and warm summers offering a variety of atmospheres throughout the year. Planning your visit around late spring or early fall can help you enjoy milder temperatures and vibrant city events, greatly enhancing your travel experience.

Dining Recommendation

When in Chicago, don’t miss the iconic deep-dish pizza at Lou Malnati's, a dish that celebrates bold flavors and a hearty, cheesy depth that contrasts with Stamford's more coastal fare. The vibrant atmosphere and dedication to local ingredients in the Windy City create a dining experience that feels distinctly different from what you would find back home.

Stamford - Chicago operators

Explore transport companies operating between Stamford and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Train Show train routes

Contact phone

877.690.5114

Website

https://new.mta.info/agency/metro-north-railroad

Train from Stamford Amtrak Station to Grand Central Terminal

Average Duration

1h 13m

Estimated price

$425-426

Contact phone

+1 800-872-7245

Website

https://www.amtrak.com/home.html

Train from Stamford Amtrak Station to New York Penn Station

Average Duration

48m

Estimated price

$6261-6262

Train from New York Penn Station to Chicago Union Station

Average Duration

19h 32m

Estimated price

$1118-9750

Contact phone

+1 800-872-7245

Website

https://www.amtrak.com/home.html

Train from Stamford Amtrak Station to New York Penn Station

Average Duration

56m

Estimated price

$6267-62600

Plane Show flights

Website

https://www.aa.com/

Plane from New York La Guardia (LGA) to Chicago O'Hare (ORD)

Average Duration

2h 46m

Estimated price

$6880-6888

Website

https://www.delta.com/

Plane from New York La Guardia (LGA) to Chicago Midway (MDW)

Average Duration

5h 5m

Estimated price

$6889-6888

Website

https://www.southwest.com/

Plane from New York La Guardia (LGA) to Chicago Midway (MDW)

Average Duration

2h 31m

Estimated price

$6885-6886

Bus Show bus routes

Contact phone

+1 214-849-8100

Website

https://www.greyhound.com/

Bus from Port Authority Bus Terminal to Baltimore Downtown Bus Station

Average Duration

3h 20m

Estimated price

$6260-9760

Bus from Baltimore Downtown Bus Station to Chicago Bus Station

Average Duration

16h 40m

Estimated price

$9700-4290

Website

https://palmlandlines.com

Bus from Indianapolis IN to Chicago IL

Average Duration

3h 20m

Estimated price

$979-6265

all-pages.other Show other routes

Website

https://www.gotobus.com/cgi-bin/ivyu.cgi?gid=657605&d=indiana-travel-express/

Other from New York to Indianapolis, IN

Average Duration

11h 15m

Estimated price

$626830-0

Stamford to Chicago: Overview of Bus, Train, Flight, and Car Trips

Traveling between Stamford and Chicago offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on a scenic road trip from Stamford to the bustling city of Chicago covering a distance of 824 miles. The journey promises an exciting blend of urban exploration and captivating landscapes, making for a memorable adventure behind the wheel. 💸 Budget-conscious travelers can rejoice as the cost of driving from Stamford to Chicago typically ranges between $140 to $220, offering flexibility to plan according to personal preferences and priorities. Whether seeking affordable pit stops or indulging in luxurious amenities along the way, there are options to suit various travel budgets. 🌆 Upon reaching Chicago after approximately 13 hours and 36 minutes of driving, prepare to immerse yourself in the vibrant culture, renowned architecture, and delectable cuisine of the Windy City. With a rich tapestry of experiences awaiting, this road trip showcases the dynamic essence of traversing from one iconic American city to another.

Average price

$140 - $220

🚆 The journey from Stamford to Chicago by train requires a transfer at New York Penn Station. The total travel time, including transfers, is approximately 21 hours and 20 minutes. 🚆 Ticket prices for the train journey between Stamford and Chicago can range from $42 to $626, depending on factors such as class of service, time of booking, and availability. Despite the duration of the trip, many travelers enjoy the convenience and relaxation of train travel between these two vibrant cities.

Departure Point

Stamford Amtrak Station

Arrival Point

Chicago Union Station

🛫 Flying from Stamford to Chicago can be a convenient and quick way to reach your destination. The direct flight from New York La Guardia Airport to Chicago Midway Airport takes just 2 hours and 25 minutes with airlines like Delta and Southwest. ✈️ If you choose to fly, you can expect a total travel time of approximately 6 hours and 20 minutes from Stamford to Chicago. This includes the time it takes to get from Stamford to New York La Guardia Airport and the flight itself. 💸 Prices for flights between Chicago and Stamford can range from $124 to $391, depending on the airline, time of booking, and availability. Make sure to check for deals and discounts to get the best value for your trip.

Departure Point

New York La Guardia Airport

Arrival Point

Chicago Midway Airport

Frequently asked questions

Find out more about the route from Stamford to Chicago.

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The distance between Stamford and Chicago is 735 miles by air. The typical travel times vary depending on the mode of transportation chosen. For example, it takes approximately 21 hours and 20 minutes by train, 5 hours and 55 minutes by taking a train to New York La Guardia and then flying to Chicago Midway, and 6 hours and 20 minutes by plane. Additionally, driving between Stamford and Chicago takes around 13 hours and 36 minutes.

For cost-effectiveness, taking the train from Stamford to Chicago is the cheapest option, with prices ranging from $40 to $650 and a travel time of 21 hours and 20 minutes. However, for a more time-efficient journey, combining a train ride to New York La Guardia and then flying to Chicago Midway is the fastest option, taking only 5 hours and 49 minutes with prices ranging from $95 to $850. It is recommended to choose the train and fly option for a quicker journey, while the train provides a more budget-friendly alternative.

The prices for a train journey between Stamford and Chicago can range from $42 to $626, depending on factors such as booking class, time of booking, and availability of discounts. It's advisable to book tickets in advance to secure lower fares or look out for promotional offers to save on travel costs. Additionally, considering alternative modes of transportation like flying or driving may offer different price points, so travelers should compare and choose the option that best fits their budget and preferences.

To travel from Stamford to Chicago without using public transportation, you can opt to drive. The road distance between the two cities is around 824 miles, and the journey typically takes about 13 hours and 36 minutes by car. You also have the flexibility to make stops along the way and enjoy the scenic route, although it's important to factor in gas and potential accommodation costs. Prices for driving from Stamford to Chicago typically range from $140 to $220, depending on factors such as fuel prices, tolls, and vehicle efficiency.

To travel from Stamford to Chicago without a car, the best option is to take a train and bus combination, which takes approximately 18 hours and 11 minutes. This route is not only convenient but also cost-effective, with tickets priced between $180 to $550, depending on the specific service provider and time of booking. By opting for this public transportation option, you can enjoy a relaxing journey while avoiding the hassle of driving long distances.

There is no direct train link between Stamford and Chicago. However, you can take a train from Stamford Amtrak Station to New York Penn Station and then transfer to another train that goes to Chicago Union Station. This journey, including transfers, typically takes around 21 hours and 20 minutes. While there may not be a direct route, this option allows you to travel between Stamford and Chicago via train with some connecting stops.

The flight between Stamford and Chicago typically takes around 2 hours and 25 minutes for a direct flight from New York La Guardia Airport to Chicago Midway Airport. The cost of a flight between the two cities can vary, with prices typically ranging from $124 to $391. It's important to check for deals and book in advance to secure the best price for your trip.

Chicago offers a wide range of accommodation options, with over 1576 hotels available for visitors to choose from. Prices for hotels in Chicago start at $67 per night, catering to various budgets and preferences. Visitors can find accommodations ranging from luxury hotels to budget-friendly options, ensuring there is something for everyone's needs and preferences during their stay in Chicago. It is recommended to book in advance to secure preferred accommodations and take advantage of any special deals or discounts available.