Boston to Chicago flight tickets
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Flight information from Boston to Chicago
Shortest flight duration
2 hr(s), 55 mins
Direct flights from Boston to Chicago
Airlines offering direct flights from Boston to Chicago, starting from .
Check airlines flying from Boston to Chicago. Direct flights take only 2 hours and 55 minutes
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Save More with the Best Flight Deals
When is the cheapest time to fly from Boston to Chicago? Compare flight prices now!
Today’s flight schedule from Boston to Chicago — last minute flight deals on Traveloka!
Explore all flight schedules from Boston to Chicago, with the fastest flight taking only 2 hours and 55 minutes
Fri, 31 Oct 2025
Sat, 1 Nov 2025
Sun, 2 Nov 2025
Airline | Departure Time | Arrival Time | Origin airport | Destination airport | |
|---|---|---|---|---|---|
 American Airlines | 05:24 | 07:25 | Boston (BOS) | Chicago (ORD) | Book flight |
 United Airlines | 06:00 | 08:00 | Boston (BOS) | Chicago (ORD) | Book flight |
American Airlines | 06:57 | 08:55 | Boston (BOS) | Chicago (ORD) | Book flight |
United Airlines | 07:25 | 09:25 | Boston (BOS) | Chicago (ORD) | Book flight |
 JetBlue Airways | 08:30 | 10:35 | Boston (BOS) | Chicago (ORD) | Book flight |
United Airlines | 09:40 | 11:40 | Boston (BOS) | Chicago (ORD) | Book flight |
United Airlines | 10:25 | 17:05 | Boston (BOS) | Chicago (ORD) | Book flight |
United Airlines | 10:40 | 12:40 | Boston (BOS) | Chicago (ORD) | Book flight |
JetBlue Airways | 15:55 | 17:55 | Boston (BOS) | Chicago (ORD) | Book flight |
United Airlines | 18:23 | 20:23 | Boston (BOS) | Chicago (ORD) | Book flight |
Travel guide to Chicago — must-visit spots and travel info
Looking for cheap flights from General Edward Lawrence Logan International Airport to Chicago? Discover the best deals for flight tickets on Traveloka! Flying from General Edward Lawrence Logan International Airport to Chicago will be more enjoyable with our exclusive Traveloka flight promo. Beside flights, you can also find discounted hotels, airport transfers, and attraction tickets from all over the world! With our complete product offering, booking one-way, round-trip, and multi-city flights will be much easier. Book now and dive into endless adventures with Traveloka!
How much does Boston to Chicago flight tickets cost?
If you are interested in flying from Boston to Chicago you can check the price through Traveloka. Normally the price starts from this varies on season and availability.
How long does it take to fly from Boston to Chicago?
Typically, it takes 2 hour and 55 minutes.
What airport serves Chicago?
Airport serving in Chicago include Chicago CHIA
Travel Tips for Your Chicago Trip
Packing Tips
- Pack light for a weekend trip, or consider a cabin bag to save on checked luggage fees.
- Don’t forget a universal travel adaptor to charge your gadgets.
Safety and Health Tips
- Stay hydrated throughout your trip
- Keep an eye on personal belongings, especially in crowded tourist areas.
Benefits of Booking with Traveloka for Boston to Chicago Flight
Did you know booking through Traveloka has many benefits tailored to your travel convenience? Here's why Traveloka is the best choice for your Boston to Chicago flight booking:
- Best Prices: Access competitive deals and discounts exclusive to Traveloka users.
- User-Friendly Tools: Use Traveloka’s price alerts and flexible date search options to uncover the best fares.
- Comprehensive Customer Support: Get assistance anytime for a smooth booking experience.
Tips for Finding the Best Flight Deals
- Book in Advance: Secure your tickets early to unlock the lowest prices.
- Travel Off-Peak: Flights are more affordable on weekdays and during non-holiday seasons.
- Set Fare Alerts: Traveloka’s price alerts notify you when ticket prices drop.
- Be Flexible: Consider early morning or late-night flights to snag cheaper fares.
About Chicago
Flight Duration | 2 hr(s) 55 mins |
Airport in Boston | |
Airport in Chicago |
Frequently Asked Questions
How much is a flight ticket from General Edward Lawrence Logan International Airport to Chicago?
Planning to take off from General Edward Lawrence Logan International Airport to Chicago? Grab your ticket on Traveloka with prices starting from , along with additional discounts & promos that can be found on our promo page.
How early should I get to the airport for a domestic & international flight?
For domestic flights, we recommend arriving at the airport at least 2 hours before your scheduled departure time. For international flights, aim to be at the airport at least 3 hours prior to ensure smooth check-in, security checks, and to account for any unexpected delays. It’s better to be early and relaxed than rushing at the last minute right?
When is the best time to buy airline tickets?
Timing is everything when it comes to grabbing airline tickets. Typically, it’s best to book around 4-6 weeks in advance for domestic flights and 2-3 months for international routes. But the prices also depend on the travel demand, seasonality, and major events. You can always monitor the fare trends on Traveloka and set alerts to catch the best deals or promotions!
What is the cheapest day to fly to Chicago?
Looking for the best deals to Chicago? Historically, midweek flights (particularly on Tuesdays and Wednesdays), tend to be cheaper due to lower demand. However, airfares can fluctuate so we recommend keeping an eye on flight prices and being flexible with your travel dates. Booking in advance can be one the hacks to travel to Chicago without breaking the bank!
What information do I need to know when booking a flight?
When booking a flight, every choice sets the tone for your trip. From the preferred flight route – be it direct or with layovers – to the in-flight experience – whether you opt for a standard economy seat or a luxurious first-class journey – and understanding baggage limits, there's a lot to weigh. Other considerations include travel insurance and the airline's booking policies.
How far in advance should I book an international flight?
For international flights, it’s wise to start your search about 5-6 months ahead with the optimal booking window being around 3-4 months before departure. This period often provides a balance between good fares and a reasonable choice of flight times and routes. But please note that several factors such as destination popularity, peak travel season, and regional major events can influence the timeline.
Do I need a passport and visa to fly between General Edward Lawrence Logan International Airport to Chicago?
Traveling from General Edward Lawrence Logan International Airport to Chicago typically requires specific documents. For international flights, a passport is almost always necessary. However, for domestic flights, neither a passport nor a visa is usually required, but an official ID will be needed. The necessity of a visa depends on the traveler's citizenship and Chicago's entry regulations. It's crucial to verify visa requirements, as rules can differ between countries.
Why should I book my flight with Traveloka?
Booking flight tickets with Traveloka can feel like diving into an ocean of options! Our platform provides the most comprehensive choices to ensure you find the perfect flight for your adventure. With our smooth booking process, you'll also be provided with a variety of payment methods. Anxious about transacting online? We've got you covered with our top-tier security for each transaction! With Traveloka, your flight booking journey becomes hassle-free!
Is there any available promo in Traveloka?
Yes, you can save 5% off on Flights, Hotels, and Attractions up to S$100 using BOOKTRAVELOKA promo code if you are a new user. The promo is only valid for bookings made through the Traveloka App only.
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