Compare fares, departure times, stops and baggage details for this route, then open the full search when you are ready to check current availability and complete booking.
BOSORDTue, 29 Sep
Fare checked before payment No hidden charges Transparent cancellation policy 24×7 booking support
Lowest fareUS$146Delta Air Lines
Fastest2h 42mgate to gate
Options found149flights on this route
Find your flightBOS → ORD
Boston to Chicago flights
Compare fares, timings and baggage. Pick the flight that suits your trip.
Prices in USD
149 flight options
Fares are checked again before payment.
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Room availability is checked live
$65per night+ taxes if applicable
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AA
American Airlines
AA-4630
06:00
2026-09-29
BOSTON (BOS)Logan International
6H :05 M
1 Stop
LGA
· 2h 01m New York (LGA), United States
11:05
2026-09-29
CHICAGO (ORD)O Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 2 Pieces
$186
Flight DetailsBOS to ORD - 6H :05 M
Baggage InfoCheck-in 0 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
AA
American Airlines
AA-1535
06:00
2026-09-29
BOSTON (BOS)Logan International
6H :41 M
1 Stop
DCA
· 2h 33m Washington (DCA), United States
11:41
2026-09-29
CHICAGO (ORD)O Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 2 Pieces
$186
Flight DetailsBOS to ORD - 6H :41 M
Baggage InfoCheck-in 0 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
AA
American Airlines
AA-4357
06:00
2026-09-29
BOSTON (BOS)Logan International
7H :14 M
1 Stop
JFK
· 3h 06m New York (JFK), United States
12:14
2026-09-29
CHICAGO (ORD)O Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 2 Pieces
$186
Flight DetailsBOS to ORD - 7H :14 M
Baggage InfoCheck-in 0 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
AA
American Airlines
AA-1540
06:00
2026-09-29
BOSTON (BOS)Logan International
7H :16 M
1 Stop
PHL
· 3h 00m Philadelphia (PHL), United States
12:16
2026-09-29
CHICAGO (ORD)O Hare International
Non Refundable 7 Seat Left Economy
Check-in: 0 PiecesCabin: 2 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 2 Pieces
$186
Flight DetailsBOS to ORD - 7H :16 M
Baggage InfoCheck-in 0 Pieces - Cabin 2 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Up to 120 of 149 options on this route. Open the full search to see them all with every filter.
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Boston to Chicago fare highlights
Selected flight highlights for 29 Sep 2026.
Lowest fare$146Delta Air Lines07:30
Earliest departure$197United Airlines05:45
Shortest duration$146Delta Air Lines20:50
Night
00:00-05:59
$197United Airlines at 05:45Morning
06:00-11:59
$146Delta Air Lines at 07:30Afternoon
12:00-17:59
$146Delta Air Lines at 16:30Evening
18:00-23:59
$146Delta Air Lines at 20:50
Boston to Chicago route details
Boston (BOS)
Logan International
USA
Chicago (ORD)
O Hare International
USA
Flights shown for 29 Sep 2026. View all flights opens the complete search result.
Smart travel dates
Holidays and peak dates for Chicago
Fares and hotel rates usually run higher around these dates. Booking earlier — or shifting a day or two — often costs less.
Busiest periods: Summer travel (15 Jun – 31 Aug), Holiday season (18 Dec – 02 Jan).
12OctColumbus DayMonday · in 31 days
12OctColumbus DayMonday · in 31 days
12OctIndigenous Peoples' DayMonday · in 31 days
11NovVeterans DayWednesday · in 61 days
26NovThanksgiving DayThursday · in 76 days
25DecChristmas DayFriday · in 105 days
Fixed-date national holidays. Festivals that follow the lunar calendar shift each year and are not listed here — check the exact date for your travel year.
Compare your journey
How to travel Boston to Chicago
Every option we can actually book for you, compared on price and journey time.
Connecting flight₹14,943Longer — includes a stop125 options
3 airlines operate this route.
Road distance and coach duration are approximate estimates from the air distance, not a timetable.
Airlines flying from Boston to Chicago
Compare fares, stops, baggage and refundability across the airlines flying this route.
AM
American Airlines Boston to Chicago flights
from $17661 flights
Fares from
$176
Non-stop
10 in these results
Departures
61 — compare timings in the list above
DE
Delta Air Lines Boston to Chicago flights
from $14655 flights
Fares from
$146
Non-stop
4 in these results
Departures
55 — compare timings in the list above
UN
United Airlines Boston to Chicago flights
from $18733 flights
Fares from
$187
Non-stop
10 in these results
Departures
33 — compare timings in the list above
Boston to Chicago flight details
Lowest fare
US$146 · Tue, 29 Sep
Fastest flight duration
2h 42m · Delta Air Lines
First departure of the day
05:45 · United Airlines
Last departure of the day
22:00 · Delta Air Lines
Options in this snapshot
149
Direct / non-stop options
24
Popular airlines on this route
American Airlines, Delta Air Lines, United Airlines
Airport codes
Boston–BOS, Chicago–ORD
Fares and timings are indicative — the exact price is confirmed with the airline when you search.
Boston to Chicago flight schedule, timing and fares
Boston to Chicago flight schedule and timing
Around 149 flights appear in the dated route snapshot, including 24 non-stop options. Departures run through the day — the first flight leaves around 05:45 and the last around 22:00. The fastest flight takes about 2h 42m.
Morning vs evening Boston–Chicago fares
Lowest fare by departure window: Morning from $146, Afternoon from $146, Evening from $146, Night from $197. These observations do not predict the cheapest departure window on other dates.
What is the cheapest flight from Boston to Chicago?
The cheapest fare we are showing right now is US$146, on a Tuesday departure. Airfares change through the day, so search your dates for the exact price.
Should I book one-way or round-trip for Boston to Chicago?
Compare the complete cost and conditions of both options for your dates. A round-trip can have different fare and change rules from two one-way tickets. One booking may contain multiple airline PNRs; confirm baggage transfer and connection protection for separate tickets.
Which airlines should I consider for Boston to Chicago?
American Airlines (61 flights, from $176), Delta Air Lines (55 flights, from $146), United Airlines (33 flights, from $187). Compare fare type, baggage and refundability — the cheapest airline is not always the best value for your dates.
Web check-in for your Boston to Chicago flight
Check the operating airline’s opening time and check-in deadline for each sector. Seat charges and availability depend on your fare. Use the airline reference and the links on Web Check-in.
How to book a Boston to Chicago flight on FlyX
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2
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5
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Boston and Chicago travel guide
About Chicago
Chicago, the most populous city in Illinois and the third most populous in the United States, is a bustling metropolis known for its iconic skyline, vibrant arts scene, and diverse neighborhoods. Often referred to as the Windy City, Chicago offers a blend of architectural marvels, cultural landmarks, and a dynamic urban atmosphere. From world-class museums to sandy beaches along Lake Michigan, Chicago is a city that captivates visitors with its charm and energy.
Read more about Chicago
Airports
Chicago is served by two major airports: • O'Hare International Airport (ORD) - Located approximately 18 miles northwest of downtown Chicago • Chicago Midway International Airport (MDW) - Situated about 10 miles southwest of the city center
Hotels and Restaurants
Chicago offers a wide range of accommodation options to suit every budget: • The Ritz-Carlton Chicago - Luxury hotel with stunning views of Lake Michigan • The Drake Hotel - Historic hotel with elegant rooms and top-notch service • Hotel Lincoln - Boutique hotel with a rooftop bar and quirky decor • HI Chicago Hostel - Budget-friendly option with modern amenities
When it comes to dining, Chicago is a food lover's paradise: • Alinea - Renowned for its innovative and artistic dishes • Lou Malnati's Pizzeria - Famous for its deep-dish pizza • Girl & the Goat - Popular spot for creative small plates • Portillo's - Iconic for its Chicago-style hot dogs
Transportation
Getting around Chicago is convenient with various transportation options: • Chicago Transit Authority (CTA) - Extensive network of buses and 'L' trains • Metra - Commuter rail system connecting the suburbs to the city • Taxis and Rideshares - Widely available across the city • Divvy Bikes - Bike-sharing program with numerous docking stations
Must-See Places
Chicago boasts numerous attractions that should not be missed: • Millennium Park - Home to the iconic Cloud Gate sculpture (The Bean) • The Art Institute of Chicago - Houses an impressive collection of artworks • Navy Pier - Entertainment hub with rides, restaurants, and shops • Willis Tower Skydeck - Offers breathtaking views from the 103rd floor • Museum Campus - Includes the Field Museum, Shedd Aquarium, and Adler Planetarium
Climate
Chicago experiences a continental climate with distinct seasons: • Winter (December to February) - Cold and snowy, ideal for winter sports • Spring (March to May) - Mild temperatures and blooming flowers • Summer (June to August) - Warm and humid, perfect for outdoor activities • Autumn (September to November) - Cool and crisp, great for sightseeing
The best time to visit Chicago is during late spring to early autumn when the weather is pleasant and outdoor events are in full swing. Whether you're exploring its architectural wonders, indulging in its culinary delights, or enjoying its vibrant cultural scene, Chicago promises an unforgettable experience.
Why book your Boston to Chicago flight with FlyX?
Compare the available Boston to Chicago options by total price, stops, baggage and fare conditions. Search your dates for current availability, then review traveller details and the final price before paying.
Payment confirmation and ticket issuance are separate steps. If your booking is awaiting a PNR or ticket, follow its status and contact FlyX support when you need help. Your issued ticket contains the airline reference and itinerary. Change and cancellation charges depend on the purchased fare and any separately disclosed service fee.
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Boston to Chicago flight offers & coupon codes
Coupon code
Offer
Max saving
FLYX20
Up to 20% Off on Flights
₹1,500
Check coupon eligibility and the final discount on the review page before you pay. View full terms.
Frequently asked questions - Boston to Chicago flights
Is it worth booking Boston to Chicago flights in advance?
There is no guaranteed cheapest booking window. Compare your planned dates early, check nearby dates and consider baggage, connection time and change conditions as well as price. Across the dates currently loaded for Boston to Chicago, Tuesday shows the lowest fare at $146. That is an observed snapshot for these dates, not a rule that holds every week.
How far is Boston from Chicago by air?
The flying distance depends on the routing the airline selects. The live flight cards above show duration and stop details for each result.
Are there non-stop flights from BOS to ORD?
Yes. 24 non-stop flights are showing on Boston to Chicago for the dates currently loaded. Use the Stops filter to see only those.
Which airlines fly Boston to Chicago?
American Airlines, Delta Air Lines and United Airlines are showing on this route for the dates currently loaded. Fares, baggage allowance and refund rules differ by airline and by fare type, so compare the fare conditions and not only the headline price.
How long is the flight from Boston to Chicago?
The quickest non-stop Boston to Chicago flight currently loaded takes about 2h 42m. Across the non-stop options showing, block time ranges from 2h 42m to 3h 20m. Journeys with a stop take longer, since the total includes the layover.
What is the cheapest Boston to Chicago flight fare?
The lowest fare showing on Boston to Chicago for the dates currently loaded is $146. Fares on the same dates run up to $310, depending on airline, timing and fare type. Airline pricing moves continuously, so treat this as a dated observation rather than a fixed price.
What time do Boston to Chicago flights depart?
For the dates currently loaded the first departure is around 05:45 and the last is around 22:00, local time at Boston. Use the departure-time filter on the results above to narrow to a morning, afternoon or evening slot.
Why does the price change after clicking Book Now?
Airline seat inventory and fares change continuously. Selecting Book Now runs a live fare verification with the airline so the price you approve is the price you pay - if it has moved, you see the new figure before any payment.
Before you book this route
Check the airport codes BOS–ORD, local departure and arrival dates, and every connecting airport. Connections can have different document and baggage requirements from your final destination.
Where these fares come from
The fares, durations, stops and baggage shown here come from real airline search results for this route. They are examples for the dates on this page, not a full timetable and not a locked price — run a search to see what is available for your own dates.
Last checked .
Check official travel requirements
Confirm passport, visa and transit rules for your nationality and full itinerary with the relevant government and operating airline. IATA travel-document information explains why requirements vary.
The BOS to ORD cards above show selected flight options. Airline prices and seat availability can move quickly, so the final fare is rechecked in the booking flow.
Before you book
Compare nearby dates
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Use filters
Shortlist by price, stops, departure time and refundable fare preference.
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Lowest Boston to Chicago airfare today, in 30 days and in 90 days
Cheapest Fare
Fare
Date
Airline
Departure
Lowest Airfare Today
$146
29/09/2026
Delta Air Lines
07:30
Cheapest Airfare Within 30 Days
$143
11/10/2026
Delta Air Lines
07:30
Cheapest Airfare Within 90 Days
$139
10/12/2026
Delta Air Lines
07:30
Book Boston to Chicago Flight Tickets on FlyX
Planning to fly from Boston to Chicago? FlyX lets you compare flight rates, airline timings, layovers, and baggage allowances all in one simple list. From quick non-stop routes to flexible connecting options, finding and booking cheap air tickets has never been easier.
Boston to Chicago Flight Schedule and Timing
Around 149 flights operate on this route, providing plenty of choices for your travel window. The earliest morning flight departs from Boston at 05:45, while the last night flight leaves at 22:00. Flights depart from Logan International and land at O Hare International.
Flight Route Details & Analysis
Flight Details
Information
Route
Boston to Chicago
Flight Duration
2H :42 M - 16H :18 M
Airport Codes
Boston - BOS, Chicago - ORD
Total Flights Available
149 flights (24 direct)
First Flight Departure
Departs at 05:45
Last Flight Departure
Departs at 22:00
Early Morning Flights (12 AM - 8 AM)
39 direct/indirect flights
Morning Flights (8 AM - 12 PM)
51 direct/indirect flights
Afternoon Flights (12 PM - 4 PM)
33 direct/indirect flights
Evening Flights (4 PM - 8 PM)
20 direct/indirect flights
Night Flights (8 PM - 12 AM)
6 direct/indirect flights
Airport Information & Terminals
BOS: Boston Logan International Airport. Logan is close to downtown Boston compared with many US airports. Taxis, airport buses and transit work well, but winter weather and academic move-in dates can change travel ease.
ORD: Chicago airport system. Chicago flights commonly use O'Hare or Midway. O'Hare is a huge hub with rail access; Midway can be easier for some city-side trips. Winter weather and traffic should be part of the booking decision.
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Logan International