Back Bay skyline across the Charles River from the Longfellow Bridge. Flights from Chicago to Boston

Route guide

Cheap Flights from Chicago to Boston

Search Chicago to Boston flights from O'Hare (ORD) to Logan (BOS), with O'Hare security hours, Terminal 5 tips and the free transit links at Logan.

ORD to BOS · 864 mi · 2h 28m est.

ORD to BOS
864 miles
2h 28m nonstop (estimated)
5 airlines in our fare results

Photo: King of Hearts, CC BY-SA 4.0, via Wikimedia Commons

Chicago to Boston flight insights

Average flight time

~2h 28m (estimated)

ORD → BOS

Cheapest cached price

$154

Checking live fares…

Prices shown may not be current. Last checked: Oct 26, 2026.

Planning a trip from Chicago to Boston? The average flight time on this route is ~2h 28m (estimated). The lowest fare we recorded on this route recently was $154 (last checked Oct 26, 2026); today's live fare for your dates can differ.

Chicago to Boston at a glance

ORD to BOS is about 864 miles in a straight line. The curved line is an illustration; the route your airline flies may differ.

Route Quick Facts

Quick facts for flights from Chicago to Boston on Eazair
Origin	Chicago (ORD)
Destination	Boston (BOS)
Average Flight Time	~2h 28m (estimated)
Current Lowest Fare	$154
Fares Last Checked	Oct 26, 2026
Distance	864 miles (ORD to BOS)
Time in Boston	1 hour ahead of Chicago
Airlines in our fare results	5

Local time in Boston is 1 hour ahead of Chicago. Chicago is on Central Time, Boston on Eastern Time.

Flight deals from Chicago to Boston

Departures for this search are from Chicago O'Hare International (ORD), not Chicago Midway (MDW), and arrivals are at Boston Logan International (BOS). For Boston, the O'Hare nonstop list dated 1 Sep 2026 names American Airlines, Delta Air Lines, United Airlines and JetBlue. Schedules change, so look at the stops shown with each result. United, American, JetBlue and Delta have appeared in EazAir's fare checks for this route.

Delta, which says its O'Hare flights moved to Terminal 5, departs from the terminal whose checkpoint O'Hare lists as open 24 hours, with PreCheck lanes there from 3:45 a.m. to 8:30 p.m. Other checkpoints keep shorter hours: CP2 in Terminal 1, with PreCheck, is listed from 4 a.m. to 8:30 p.m., and Terminal 2's checkpoint from 3:15 a.m. to 11 p.m. O'Hare warns that day-to-day airport activities can affect these. Off the CTA Blue Line, Basement Level tunnels lead to Terminals 1, 2 and 3.

At Logan, the free Massport Shuttle collects passengers at every terminal and runs to Airport station on the MBTA Blue Line, where a fare applies. From there, change at State for the Orange Line or at Government Center for the Green Line. The MBTA sells CharlieTickets and CharlieCards at fare machines in the Logan terminals, and riders can also tap a contactless card or phone. American lists Terminal B at Logan, gates B4 to B22.

Sixteen checks for ORD to BOS, the first EazAir has stored, were taken between 13 Sep and 12 Oct 2026, and each noted the cheapest one-way economy fare partner sites returned for one adult departing 30 days later. Those 16 gave 10 different results, the top at least double the bottom, and the lowest appeared on 17 Sep. On United Basic Economy, United picks the seat before boarding and no checked bag is included. Search your own dates, and check the final price, bags and fare rules on the partner site before you pay.

Airports for Chicago to Boston flights

Departure · Chicago

O'Hare International (ORD)

Central Time

Other airports near Chicago: Chicago Midway International (MDW)

Arrival · Boston

Logan International (BOS)

Eastern Time

About Boston

Areas to know in Boston

Back Bay
North End
Beacon Hill

Weather in Boston

Four distinct seasons: cold, snowy winters and warm, humid summers, with fall foliage drawing visitors through October.

Chicago to Boston: airport and fare guide

Checked on 17 Oct 2026 against the airport, airline and transit pages listed under Sources. Airports and airlines change these details, so confirm them with your airline before you fly.

Chicago O'Hare International's nonstop list (as of 1 Sep 2026) shows Boston (BOS) served by American Airlines, Delta Air Lines, United Airlines and JetBlue. Schedules change, so check the stops shown with each result.

TF Green Airport is a separate airport. The MBTA says the Providence/Stoughton Commuter Rail line from South Station connects to it.

Chicago Midway (MDW) is a separate airport, served by the CTA Orange Line. Check which Chicago airport each fare uses.

Leaving from Chicago O'Hare International (ORD)

The CTA Blue Line runs 24 hours to O'Hare station, which links to Terminals 1, 2 and 3 by Basement Level tunnels. For Terminal 5, ride the free Airport Transit System from Terminal 2.
Pace Routes 250 and 330 and Metra North Central Service weekday trains stop at the Multi-Modal Facility, which the Airport Transit System links to every terminal.
O'Hare lists the Terminal 5 checkpoint (CP10) as open 24 hours, with TSA PreCheck from 3:45 a.m. to 8:30 p.m. Terminal 2's checkpoint (CP5) is listed from 3:15 a.m. to 11 p.m., with PreCheck from 3:30 a.m. to 8 p.m.
In Terminal 1, CP1 is listed from 3:30 a.m. to 11 p.m. and CP2, with TSA PreCheck, from 4 a.m. to 8:30 p.m. In Terminal 3, CP7A is listed from 3:30 a.m. to 10:30 p.m., with PreCheck from 3:30 a.m. to 8:30 p.m.
O'Hare says checkpoint hours may be affected by day-to-day airport activities, and recommends checking with your airline about operations on the date of your flight.

Arriving at Boston Logan International (BOS)

Airline	Logan terminal
American	Terminal B, gates B4 to B22.
Delta	Terminal A and Terminal E for domestic flights. Check the Fly Delta app or My Trips for yours.
JetBlue	Terminal C for domestic flights and international departures. International arrivals use Terminal E.
Other airlines	Check your boarding pass or airline app.

Taken from each airline's own page on 17 Oct 2026, as Massport's airline list could not be checked. Terminals can change, so confirm yours with your airline.

The MBTA says the Silver Line SL1 bus and the free Massport Shuttle stop at every Logan terminal.
Delta runs a shuttle bus between Terminal A, near gates A13 to A22, and Terminal E, normally at gate E13, from 4:30 a.m. to 10:30 p.m. daily.
JetBlue lists Terminal C for its domestic flights and international departures, and Terminal E for international arrivals.

Getting from BOS	Where to board	Where it goes
MBTA Silver Line SL1	Stops at every Logan terminal. The MBTA says service from the airport is always free.	South Station, for the Red Line and Commuter Rail.
Massport Shuttle and MBTA Blue Line	The free Massport Shuttle picks up at every terminal and runs to Airport station. A fare applies on the Blue Line.	State and Government Center. Change at State for the Orange Line or at Government Center for the Green Line.
MBTA Silver Line SL3	Airport station, reached on the free Massport Shuttle.	Chelsea, with Commuter Rail and bus connections at Chelsea station.
MBTA ferry	Logan Airport Ferry Terminal. Buy tickets at fare machines, in the mTicket app, or on board.	Long Wharf, Lovejoy Wharf (North Station), Hingham and Hull, with more service in summer.

What the lowest fares include

Fare	Carry-on	Checked bag	Seat	Changes
Delta Main Basic	Delta says every passenger can bring one carry-on and one personal item free.	Delta charges for checked bags on domestic flights unless you qualify for a waiver, such as Medallion status or an eligible Delta SkyMiles American Express card.	Assigned after check-in. You may be able to buy a seat ahead of time for a fee.	Refunds are not allowed after the 24-hour risk-free cancellation window. Delta says a change or cancellation may be possible for a fee, with any value left as an eCredit.
American Basic Economy	Included, plus a personal item.	Not included, except for some AAdvantage status members and eligible cardmembers.	A free seat is assigned at check-in, or you can pay to choose one.	Generally not allowed. American describes a 24-hour window and some credit options on its Basic Economy page.
United Basic Economy	Not included on domestic flights. One personal item only, unless you are a MileagePlus Premier member, travel with one, or hold a qualifying MileagePlus card.	Not included; check United's bag fee calculator.	Assigned by United before boarding.	Changes may not be allowed. Refund if cancelled within 24 hours of booking, under United's 24-hour policy; after that, partial travel credit.
JetBlue Main Base (bookings made after 29 Jul 2026)	Included, plus a personal item.	Not included.	Costs extra.	Change fee plus any fare difference. Cancelling gives travel credit minus a fee.

Based on the airlines' own pages, checked on 17 Oct 2026. Fees are left out because they change often. Check the final price, bags and fare rules on the partner site before you pay.

How EazAir measured fares on this route

EazAir's first 16 fare checks from Chicago to Boston ran from 13 Sep to 12 Oct 2026. For the return direction, Boston to Chicago, EazAir's first 14 checks ran from 12 Sep to 15 Oct 2026. Each check asked partner travel sites for the lowest one-way economy fare for one adult, departing 30 days after the check. Results can include connecting flights. The highest result was at least double the lowest. The 16 checks returned 10 different results. The lowest result came on 17 Sep. That is a small sample, so it shows that prices move, not when they are lowest. Search your own dates for current prices.

Sources

Delta: Delta's new O'Hare home (11 Oct 2022, accessed 17 Oct 2026)
O'Hare: Public transit (no date shown, accessed 17 Oct 2026)
CTA: Airports (no date shown, accessed 17 Oct 2026)
O'Hare: ATS service update (no date shown, accessed 17 Oct 2026)
O'Hare: TSA checkpoints (no date shown, accessed 17 Oct 2026)
O'Hare: Domestic nonstop destinations (as of 1 Sep 2026, accessed 17 Oct 2026)
MBTA: Logan Airport (no date shown, accessed 17 Oct 2026)
JetBlue: Boston airport information (no date shown, accessed 17 Oct 2026)
Delta: Boston airport update (no date shown, accessed 17 Oct 2026)
American: Boston airport information (no date shown, accessed 17 Oct 2026)
Southwest: Airport information, Boston Logan (no date shown, accessed 17 Oct 2026)
Delta: Delta Main Basic (no date shown, accessed 17 Oct 2026)
Delta: Fares and discounts (no date shown, accessed 17 Oct 2026)
Delta: Carry-on baggage (no date shown, accessed 17 Oct 2026)
Delta: Bags (no date shown, accessed 17 Oct 2026)
American Airlines: Basic Economy (no date shown, accessed 17 Oct 2026)
United: Basic Economy FAQ (no date shown, accessed 17 Oct 2026)
JetBlue: Fare options (no date shown, accessed 17 Oct 2026)
EazAir fare checks for ORD to BOS, 13 Sep 2026 to 12 Oct 2026; BOS to ORD, 12 Sep 2026 to 15 Oct 2026

Frequently asked questions

When is TSA PreCheck open at O'Hare Terminal 5?

O'Hare lists the Terminal 5 checkpoint as open 24 hours, with TSA PreCheck from 3:45 a.m. to 8:30 p.m. O'Hare says checkpoint hours may be affected by day-to-day airport activities.

How do I reach O'Hare on the CTA Blue Line?

The Blue Line runs 24 hours to O'Hare station, which links to Terminals 1, 2 and 3 by Basement Level tunnels. For Terminal 5, ride the free Airport Transit System from Terminal 2.

Is the bus from Logan free?

The MBTA says Silver Line SL1 service from Logan Airport is always free. The SL1 stops at every terminal and runs to South Station, which connects with the Red Line and Commuter Rail.

Which Boston terminal does JetBlue use?

JetBlue lists Terminal C at Logan for domestic flights. Delta's domestic flights use Terminal A or Terminal E, and American lists Terminal B. Terminals can change, so confirm yours with your airline.

Can I bring a carry-on on the lowest fares from Chicago to Boston?

On Delta Main Basic, American Basic Economy and JetBlue Main Base, yes, along with a personal item. United Basic Economy includes only a personal item on domestic flights, apart from some MileagePlus members and cardholders.

How far is Chicago from Boston?

ORD and BOS are about 864 miles apart in a straight line. Flight times vary by airline, direction and routing, so check the scheduled time shown with each result.

Airline bag fees

Baggage allowances differ significantly between fare classes (Basic/Light vs. Standard/Flex) and can change over time. Always verify the exact allowance for your specific fare with the airline before you fly.

Checked bag fees from each airline's own website
Airline	Carry-on, basic economy	1st checked bag	2nd checked bag	Source
American Airlines	Included	$45	$55	aa.com, Sep 24, 2026
United Airlines	Not included	$40	$50	united.com, Sep 24, 2026
Delta Air Lines	Included	$45	$55	delta.com, Sep 24, 2026
Southwest Airlines	Included	$45	$55	southwest.com, Oct 27, 2026
JetBlue	Included	$45	$59	jetblue.com, Sep 24, 2026
Alaska Airlines	Included	$45	$55	alaskaair.com, Sep 24, 2026
Frontier Airlines	Not included	Varies	Varies	flyfrontier.com, Sep 24, 2026
Sun Country Airlines	Not included	Varies	Varies	suncountry.com, Sep 24, 2026

Domestic US fees per bag, each way, when paid online in advance. "Varies" means the airline prices bags by route and date.

Travel tips

Arrive early for domestic flights

TSA generally recommends arriving at least 2 hours before a domestic departure, more at larger hub airports during peak travel periods.

Pack a mixed carry-on

Keep a change of clothes, chargers, and any essentials in your carry-on rather than only your checked bag, in case of a delay or a bag that doesn't arrive with you.

Screenshot your confirmation

Save a screenshot or PDF of your booking confirmation and boarding pass before you travel, in case you lose signal or battery at the airport.

Check in online when it opens

Most airlines open online check-in 24 hours before departure. Checking in early can help with seat selection and, on some airlines, boarding group assignment.