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.
ORDBOSSat, 03 Oct
Fare checked before payment No hidden charges Transparent cancellation policy 24×7 booking support
Lowest fareUS$147Delta Air Lines
Fastest2h 24mgate to gate
Options found115flights on this route
Find your flightORD → BOS
Available Flights & Fares
Compare fares, timings and baggage. Pick the flight that suits your trip.
Prices in USD
115 flight options
Fares are checked again before payment.
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La Quinta Inn & Suites by Wyndham Boston Somerville
23 Cummings St SomervilleMassachusetts 02145 ,
Room availability is checked live
$204per night+ taxes if applicable
1 Night • 3 Star
United Airlines
UA-1027
06:00
2026-10-03
CHICAGO (ORD)O Hare International
5H :43 M
1 Stop
EWR
· 2h 15m New York (EWR), United States
12:43
2026-10-03
BOSTON (BOS)Logan International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 1 Pieces
$197
Flight DetailsORD to BOS - 5H :43 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Non Refundable
Fare Type
AirLine Private
0 Pieces 1 Pieces
$543
Flight DetailsORD to BOS - 5H :43 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
United Airlines
UA-1077
07:00
2026-10-03
CHICAGO (ORD)O Hare International
6H :55 M
1 Stop
DCA
· 3h 11m Washington (DCA), United States
14:55
2026-10-03
BOSTON (BOS)Logan International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 1 Pieces
$197
Flight DetailsORD to BOS - 6H :55 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Non Refundable
Fare Type
AirLine Private
0 Pieces 1 Pieces
$543
Flight DetailsORD to BOS - 6H :55 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
United Airlines
UA-1273
07:30
2026-10-03
CHICAGO (ORD)O Hare International
6H :05 M
1 Stop
EWR
· 2h 25m New York (EWR), United States
14:35
2026-10-03
BOSTON (BOS)Logan International
Non Refundable 4 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 1 Pieces
$197
Flight DetailsORD to BOS - 6H :05 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Non Refundable
Fare Type
AirLine Private
0 Pieces 1 Pieces
$543
Flight DetailsORD to BOS - 6H :05 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
United Airlines
UA-2277
08:50
2026-10-03
CHICAGO (ORD)O Hare International
5H :05 M
1 Stop
IAD
· 1h 15m Washington (IAD), United States
14:55
2026-10-03
BOSTON (BOS)Logan International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 1 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 1 Pieces
$197
Flight DetailsORD to BOS - 5H :05 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Non Refundable
Fare Type
AirLine Private
0 Pieces 1 Pieces
$543
Flight DetailsORD to BOS - 5H :05 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
No flights match the selected filters. Clear filters or open full search.
Today's Airfare Highlights
Selected flight highlights for 03 Oct 2026.
Lowest fare$147Delta Air Lines07:30
Earliest departure$197United Airlines05:00
Shortest duration$187United Airlines06:10
Night
00:00-05:59
$197United Airlines at 05:00Morning
06:00-11:59
$147Delta Air Lines at 07:30Afternoon
12:00-17:59
$147Delta Air Lines at 16:35Evening
18:00-23:59
$167Delta Air Lines at 18:00
Departure & Arrival Airport Details
Chicago (ORD)
O Hare International
USA
Boston (BOS)
Logan International
USA
Flights shown for 03 Oct 2026. View all flights opens the complete search result.
Smart travel dates
Holidays and peak dates for Boston
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 30 daysPeak
12OctColumbus DayMonday · in 30 daysPeak
12OctIndigenous Peoples' DayMonday · in 30 daysPeak
11NovVeterans DayWednesday · in 60 days
26NovThanksgiving DayThursday · in 75 days
25DecChristmas DayFriday · in 104 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 Chicago to Boston
Every option we can actually book for you, compared on price and journey time.
Connecting flight₹15,963Longer — includes a stop92 options
3 airlines operate this route.
Road distance and coach duration are approximate estimates from the air distance, not a timetable.
Airlines flying from Chicago to Boston
Compare fares, stops, baggage and refundability across the airlines flying this route.
AM
American Airlines Flights
from $19754 flights
Fares from
$197
Non-stop
10 in these results
Departures
54 — compare timings in the list above
UN
United Airlines Flights
from $18738 flights
Fares from
$187
Non-stop
10 in these results
Departures
38 — compare timings in the list above
DE
Delta Air Lines Flights
from $14723 flights
Fares from
$147
Non-stop
3 in these results
Departures
23 — compare timings in the list above
Route Overview & Flight Facts
Fastest flight duration
2h 24m · United Airlines
First departure of the day
05:00 · United Airlines
Last departure of the day
21:24 · United Airlines
Options in this snapshot
115
Direct / non-stop options
23
Airport codes
Chicago–ORD, Boston–BOS
Fares and timings are indicative — the exact price is confirmed with the airline when you search.
Flight Schedule, Timings & Airfare Insights
Daily Flight Schedule & Travel Duration
Around 115 flights appear in the dated route snapshot, including 23 non-stop options. Departures run through the day — the first flight leaves around 05:00 and the last around 21:24. The fastest flight takes about 2h 24m.
Morning vs Evening Departure Fares
Lowest fare by departure window: Morning from $147, Afternoon from $147, Evening from $167, Night from $197. These observations do not predict the cheapest departure window on other dates.
Cheapest Airfare & Best Time to Book
Search your travel dates to compare current fares — prices update continuously with airline inventory.
One-Way vs Round-Trip Fare Comparison
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.
Online Web Check-In & Boarding Pass
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 Cheap Flights on FlyX
1
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2
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Sort or filter the Chicago–Boston results by price, departure time, stops and airline.
3
Open the fare choices
Check baggage allowance and refundability for each fare type before continuing.
4
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5
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Destination & City 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 Flight with FlyX?
Compare the available Chicago to Boston 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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Frequently Asked Questions
Is it worth booking Chicago to Boston 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 Chicago to Boston, Saturday shows the lowest fare at $147. That is an observed snapshot for these dates, not a rule that holds every week.
How far is Chicago from Boston 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 ORD to BOS?
Yes. 23 non-stop flights are showing on Chicago to Boston for the dates currently loaded. Use the Stops filter to see only those.
Which airlines fly Chicago to Boston?
American Airlines, United Airlines and Delta Air Lines 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 Chicago to Boston?
The quickest non-stop Chicago to Boston flight currently loaded takes about 2h 24m. Across the non-stop options showing, block time ranges from 2h 24m to 2h 47m. Journeys with a stop take longer, since the total includes the layover.
What is the cheapest Chicago to Boston flight fare?
The lowest fare showing on Chicago to Boston for the dates currently loaded is $147. Fares on the same dates run up to $631, 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 Chicago to Boston flights depart?
For the dates currently loaded the first departure is around 05:00 and the last is around 21:24, local time at Chicago. 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 ORD–BOS, 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 ORD to BOS 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
The date strip opens the complete search result for the route and selected date.
Use filters
Shortlist by price, stops, departure time and refundable fare preference.
Check fare choices
Continue to Booking opens the verified fare choices, including baggage and refundability, before review.
Lowest Chicago to Boston airfare today, in 30 days and in 90 days
Cheapest Fare
Fare
Date
Airline
Departure
Lowest Airfare Today
$147
03/10/2026
Delta Air Lines
07:30
Cheapest Airfare Within 30 Days
$144
12/10/2026
Delta Air Lines
07:30
Cheapest Airfare Within 90 Days
$140
11/12/2026
Delta Air Lines
07:30
Book Chicago to Boston Flight Tickets on FlyX
Planning to fly from Chicago to Boston? 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.
Chicago to Boston Flight Schedule and Timing
Around 115 flights operate on this route, providing plenty of choices for your travel window. The earliest morning flight departs from Chicago at 05:00, while the last night flight leaves at 21:24. Flights depart from O Hare International and land at Logan International.
Flight Route Details & Analysis
Flight Details
Information
Route
Chicago to Boston
Flight Duration
2H :24 M - 16H :10 M
Airport Codes
Chicago - ORD, Boston - BOS
Total Flights Available
115 flights (23 direct)
First Flight Departure
Departs at 05:00
Last Flight Departure
Departs at 21:24
Early Morning Flights (12 AM - 8 AM)
32 direct/indirect flights
Morning Flights (8 AM - 12 PM)
38 direct/indirect flights
Afternoon Flights (12 PM - 4 PM)
27 direct/indirect flights
Evening Flights (4 PM - 8 PM)
16 direct/indirect flights
Night Flights (8 PM - 12 AM)
2 direct/indirect flights
Airport Information & Terminals
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.
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.
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O Hare International