New Haven, CT, USA to Chicago, IL, USA from $38: 10 ways by bus, train, flight or car

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

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$38 by trainBest price

1230 kmDistance

4h 23m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from New Haven 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 New Haven to Chicago

This journey from New Haven to Chicago takes you from the charming coastal vibe of Connecticut to the vibrant city life of Illinois, each offering distinct flavors and experiences.

Best Neighborhoods in Chicago

Chicago boasts diverse neighborhoods, each offering unique experiences for visitors.

Wicker Park

• Known for its trendy boutiques and vibrant street art.

• Home to eclectic dining and music venues.

Lincoln Park

• Features beautiful parks and Lake Michigan views.

• Offers family-friendly attractions and nightlife options.

River North

• Renowned for its art galleries and upscale dining.

• Close to landmarks like the Magnificent Mile.

Best Times To Visit Chicago's Attractions

Maximize your enjoyment with these tips on when to explore Chicago's top sights.

The Art Institute of Chicago

Visit on weekdays early in the morning for a quieter experience.

Millennium Park

Go in the late afternoon, especially on weekdays, to dodge crowds.

Willis Tower Skydeck

Schedule your visit during off-peak hours, like early or late in the day.

Chicago Weather: What to Expect Year-Round

Chicago experiences a diverse climate with cold winters and warm summers, making it vital to plan your visit accordingly. Spring and fall offer mild weather, ideal for exploring the city's attractions while avoiding the heat and snow.

Dining Recommendation in Chicago

Indulge in Chicago's iconic deep-dish pizza at Giordano's, where the rich flavors and hearty layers create a fulfilling contrast to New Haven's famed thin-crust pies. The lively atmosphere and emphasis on local ingredients bring a vibrant energy to your dining experience that sets Chicago apart.

New Haven - Chicago operators

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

Train Show train routes

Contact phone

+1 800-872-7245

Website

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

Train from New Haven to Windsor Locks

Average Duration

1h 2m

Estimated price

$7596-4833

Train from New Haven to New York Penn Station

Average Duration

1h 34m

Estimated price

$48356-4834

Train from New Haven to Stamford

Average Duration

48m

Estimated price

$759-4836

Train from New Haven to Springfield

Average Duration

1h 21m

Estimated price

$4835-7596

Train from Springfield to Chicago Union Station

Average Duration

19h 46m

Estimated price

$7590-7594

Train from New York Penn Station to Chicago Union Station

Average Duration

19h 32m

Estimated price

$750-483590

Plane Show flights

Website

https://www.aveloair.com

Plane from New Haven to Chicago Midway

Average Duration

2h 25m

Estimated price

$7592-4834

Website

delta.com

Plane from Hartford to Chicago Midway

Average Duration

4h 31m

Estimated price

$7595-75920

Plane from Hartford to Chicago O'Hare

Average Duration

4h 42m

Estimated price

$7596-7597

Bus Show bus routes

Contact phone

1-800-343-9999

Website

https://peterpanbus.com

Bus from Union Station, New Haven, CT to Port Authority Bus Terminal

Average Duration

1h 35m

Estimated price

$6792-7590

Bus from Port Authority Bus Terminal to Indianapolis Bus Station

Average Duration

17h 10m

Estimated price

$7595-7570

Bus from Indianapolis IN to Chicago IL

Average Duration

3h 20m

Estimated price

$7598-4836

Contact phone

+1 214-849-8100

Website

https://www.greyhound.com/

Bus from New Haven Bus Stop to Port Authority Bus Terminal

Average Duration

2h 10m

Estimated price

$6790-750

Bus from Port Authority Bus Terminal to Indianapolis Bus Station

Average Duration

17h 10m

Estimated price

$7595-7570

Drive

Drive from New Haven to Chicago

Average Duration

14h 25m

Estimated price

$858-859

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

Traveling between New Haven 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 New Haven to Chicago covering a distance of 863 miles. Enjoy the journey through picturesque landscapes and charming small towns along the way. 💰 Discover budget-friendly options for your Chicago adventure, with car travel costs ranging from $150 to $230. Plan your budget accordingly and make the most of your road trip experience. 🌆 After approximately 14 hours and 25 minutes of driving, arrive in vibrant Chicago. Explore the city's iconic attractions, indulge in deep-dish pizza, and immerse yourself in the bustling urban culture of the Windy City.

Average price

$150 - $230

🚉 The train services from New Haven to Chicago are operated by Amtrak, providing a comfortable and relaxing travel experience for passengers. The total duration of the journey, including transfers, is approximately 22 hours and 7 minutes. 💰 Depending on the class of service and time of booking, the ticket prices for the train from New Haven to Chicago can range from $38 to $483, offering flexibility for travelers with varying budgets. Whether for business or leisure, this train route offers a unique way to discover the beauty of the East Coast and the Midwest.

Departure Point

New Haven station

Arrival Point

Chicago Union Station

Useful tips for train travellers

• Enjoy the catering services offered on board via Amtrak, which include a café car serving a variety of food and beverage options such as breakfast sandwiches, salads, snacks, and hot meals. For a full dining experience, opt for the dining car service if you're traveling in First Class, where you can enjoy complimentary meals.

• On Amtrak's service from New Haven to Chicago, you have different seating options: First Class offers roomier seats with better amenities and complimentary meals; Business Class provides comfortable seating with more legroom, and Economy Class offers affordable fares with standard seating. Each class has its own advantages depending on your budget and comfort preference.

• The main operator for this route is Amtrak. You can view schedules and book tickets on their website: amtrak.com Another option is the Night Train, which sometimes has connections for overnight travel, available on nighttrains.com Additionally, for local transportation and schedules in Chicago, check transitchicago.com

• Upon arriving at Chicago Union Station, you'll find ample amenities, including restrooms and places to grab a quick bite. Union Station also offers a luggage service where you can check your bags if you want to explore the city without carrying your luggage. Showers are not available, but various nearby hotels and gyms may offer them.

• The fastest way to get from Chicago Union Station to the city center is via the CTA's 'L'. You can catch the Pink Line from 18th Station right outside Union Station. Alternatively, the #60 bus also stops right outside and connects you to various points in the downtown area.

🛫 Embark on a quick and convenient journey from New Haven to Chicago with a direct flight from Hartford Airport to Chicago Midway Airport, taking just 2 hours and 30 minutes. 💸 Enjoy competitive pricing for your flight between Chicago and New Haven, with tickets ranging from $58 to $378, making air travel a cost-effective option for your trip.

Departure Point

Hartford Airport

Arrival Point

Chicago Midway Airport

🛣️ The entire bus trip from New Haven to Chicago, including transfers, typically takes around 23 hours and 49 minutes. Both Peter Pan Bus Lines and Palmland Bus Lines operate services on this route, providing a comfortable and convenient way to reach your destination.

Departure Point

Union Station, New Haven, CT

Arrival Point

Chicago IL station

Frequently asked questions

Find out more about the route from New Haven to Chicago.

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The distance between New Haven and Chicago is approximately 764 miles or 863.3 miles by road. The typical travel times by various modes of transportation are as follows: it takes 22 hours and 7 minutes by train, 6 hours and 22 minutes by taking a train to New York La Guardia and then flying to Chicago Midway, 14 hours and 25 minutes by car, and 17 hours and 28 minutes by bus to travel between the two cities.

The most cost-effective option for traveling from New Haven to Chicago is by train, with prices ranging from $35 to $490. This mode of transportation takes approximately 22 hours and 7 minutes. If time is a priority, the quickest option is to take a combination of train and flight, which takes around 5 hours and 59 minutes and costs between $110 and $800.

The prices for a train ticket between New Haven and Chicago can range from $38 to $483, depending on the class and type of ticket. On the other hand, the prices for a bus ticket between Chicago and New Haven can vary from $22 to $185, depending on the bus company and seating option. It is recommended to check different providers and book in advance to get the best and most affordable options.

To travel from New Haven to Chicago without using public transportation, you can drive the distance of approximately 863 miles. It usually takes around 14 hours and 25 minutes to drive from New Haven to Chicago. The cost of gas and tolls for this journey ranges from $150 to $230 depending on the vehicle and current prices.

To travel from New Haven to Chicago without a car, the best option is to take a bus. The journey typically takes around 17 hours and 28 minutes. The cost of a bus ticket can range from $21 to $190, depending on the specific bus company and the time of booking.

Yes, there is a transportation link between New Haven and Chicago. Travelers can take a train from New Haven to Chicago, with a transfer in Springfield. The journey takes approximately 22 hours and 7 minutes. Alternatively, buses are available from New Haven to Chicago, with transfers in New York, Ithaca, and other locations, with a total travel time of about 17 hours and 28 minutes.

The flight between New Haven and Chicago typically takes around 2 hours and 15 minutes. The quickest option is a direct flight from New York La Guardia Airport to Chicago Midway Airport. As for the cost, it can vary depending on factors such as airline, time of year, and how far in advance you book. On average, a round trip flight can range from $150 to $300.

There are plenty of options for accommodation near Chicago. With over 1116 hotels available, you can choose from a range of options to suit your budget and preferences. Prices start at $58 per night, offering affordable choices for travelers. Whether you're looking for luxury hotels, budget-friendly options, or something in between, you'll be able to find a suitable place to stay in Chicago.

New Haven, CT, USA to Chicago, IL, USA from $38: 10 ways by bus, train, flight or car

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

Compare Train, Bus, Flight, and Driving Options

See more options

Traveling From New Haven to Chicago

Best Neighborhoods in Chicago

Best Times To Visit Chicago's Attractions

Chicago Weather: What to Expect Year-Round

Dining Recommendation in Chicago

New Haven - Chicago operators

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

Useful tips for train travellers

Frequently asked questions

Trips from New Haven

Trips to Chicago

Popular routes