Chicago skyline at sunrise reflected in Lake Michigan. Flights from Boston to Chicago

Route guide

Cheap Flights from Boston to Chicago

Compare Boston to Chicago flights from Logan (BOS) into O'Hare (ORD), with Delta's Terminal 5 move, Blue Line steps and the Midway difference explained.

BOS to ORD · 864 mi · 2h 28m est.

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

Photo: Daniel Schwen, CC BY-SA 4.0, via Wikimedia Commons

Boston to Chicago flight insights

Average flight time

~2h 28m (estimated)

BOS → ORD

Cheapest cached price

$139

Checking live fares…

Last checked Nov 6, 2026

Planning a trip from Boston to Chicago? The average flight time on this route is ~2h 28m (estimated). The lowest fare we recorded on this route recently was $139 (last checked Nov 6, 2026); today's live fare for your dates can differ.

Boston to Chicago covers a straight-line distance of about 864 miles. Based on that distance, a nonstop flight would take approximately ~2h 28m (estimated). Actual flight time varies by airline, aircraft and routing.

Boston to Chicago at a glance

BOS to ORD 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 Boston to Chicago on Eazair
Origin	Boston (BOS)
Destination	Chicago (ORD)
Average Flight Time	~2h 28m (estimated)
Current Lowest Fare	$139
Fares Last Checked	Nov 6, 2026
Distance	864 miles (BOS to ORD)
Time in Chicago	1 hour behind Boston
Airlines in our fare results	5

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

Flight deals from Boston to Chicago

Fares on this page run into Chicago O'Hare International (ORD) from Boston Logan International (BOS). Midway (MDW), on the CTA Orange Line, is a different Chicago airport and is not searched. According to O'Hare's nonstop list (as of 1 Sep 2026), Boston is served by American Airlines, Delta Air Lines, United Airlines and JetBlue, but timetables move, so read the number of stops on each result. American, United, Delta and JetBlue have appeared in EazAir's fare checks for this route.

Delta's domestic flights at Logan use both Terminal A and Terminal E, and Delta runs a shuttle bus between Terminal A, near gates A13 to A22, and Terminal E, normally gate E13. JetBlue lists Terminal C for domestic flights. If you live along the Silver Line SL3, it runs from Chelsea to Airport station, where the free Massport Shuttle continues to every terminal.

Delta flyers land in Terminal 5, which Delta says has held its O'Hare flights since October 2022. That terminal has no rideshare pickup on O'Hare's list; app rides meet passengers upstairs at Terminal 2 or Terminal 3, and taxis queue on the lower-level curb outside baggage claim at every terminal. For the train, take the free Airport Transit System to Terminal 2 and follow signs to the CTA Blue Line, which runs 24 hours and reaches downtown in 40 to 45 minutes, CTA says.

Fourteen checks so far: EazAir's first 14 for BOS to ORD were made from 12 Sep to 15 Oct 2026, each capturing the cheapest one-way economy fare that partner sites returned for one adult flying 30 days later. Across them came 11 different results; the top one was at least double the bottom, and the lowest result came on 17 Sep. American Basic Economy keeps a carry-on and gives a free seat at check-in. Search your own dates, and check the final price, bags and fare rules on the partner site before you pay.

Airports for Boston to Chicago flights

Departure · Boston

Logan International (BOS)

Eastern Time

Arrival · Chicago

O'Hare International (ORD)

Central Time

Other airports near Chicago: Chicago Midway International (MDW)

About Chicago

Areas to know in Chicago

Wicker Park
The Loop
Lincoln Park

Weather in Chicago

Summers are warm and humid, winters are cold with lake-effect snow off Lake Michigan. Spring and fall bring the mildest sightseeing weather.

Boston to Chicago: 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.

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

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

Leaving from 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.

The SL1 bus stops at every Logan terminal, and the MBTA says transfers from the Red Line to the SL1 are free when you head to the airport.
On the Blue Line, get off at Airport station and take the free Massport Shuttle, which stops at every terminal.
MBTA ferries serve the Logan Airport Ferry Terminal from Long Wharf, Lovejoy Wharf, Hingham and Hull, with more service in summer.
JetBlue asks travelers at Logan to arrive 2 hours before domestic flights and 3 hours before international flights.
Delta says its domestic flights leave from both Terminal A and Terminal E, so check the Fly Delta app or My Trips before you go through security.
JetBlue lists Logan ticket counter hours of 2:30 a.m. to 11:30 p.m. American lists its Terminal B ticket counters as open daily from 3 a.m. to 9 p.m.
When the E3 checkpoint in Terminal E opened, TSA said it had seven screening lanes and that the E2 checkpoint would serve as overflow when volumes are heavy.

Arriving at Chicago O'Hare International (ORD)

O'Hare's airline list did not load on 17 Oct 2026. Delta says it uses Terminal 5. For other airlines, check your boarding pass or airline app.

Delta says it moved its O'Hare flights to Terminal 5 in October 2022.
The Airport Transit System train runs 24 hours, every 3 to 5 minutes at busy times, and links Terminals 1, 2, 3 and 5 with the Multi-Modal Facility for rental cars, Economy Parking Lot F, Pace buses and Metra.
From 11:30 a.m. to 9:30 p.m., a Terminal Transfer Bus runs about every 15 minutes inside security between Terminal 5 and Terminals 1 and 3, for connecting passengers with a same-day boarding pass.
At other times, passengers connecting between Terminal 5 and Terminals 1, 2 and 3 leave security, ride the Airport Transit System and are screened again.

Getting from O'Hare	Where to board	Where it goes
CTA Blue Line	Station on the lower level of the parking garage. From Terminals 1, 2 and 3, follow the Trains to City signs through the Basement Level tunnels. From Terminal 5, ride the free Airport Transit System to Terminal 2 first. Runs 24 hours. Rides starting at O'Hare cost more than a standard CTA fare.	Downtown Chicago in 40 to 45 minutes, according to CTA.
Rideshare	Upper level at Terminal 2 (orange poles 2A to 2G, with an indoor waiting area between vestibules 2A and 2D) and Terminal 3 (green poles 3G to 3K). O'Hare lists no Terminal 5 pickup, so check your app.	Wherever you booked.
Taxis	Stands on the lower-level curb outside baggage claim at each terminal.	Your destination.
Pace Routes 250 and 330	Multi-Modal Facility, bus bays 8 and 9. Ride the Airport Transit System from the terminals.	Route 250 to the Des Plaines Metra station and downtown Evanston. Route 330, on weekdays and Saturdays, to Archer Ave and Harlem Ave in Summit.
Metra North Central Service	O'Hare Transfer station, behind the Multi-Modal Facility at its northeast corner. Ride the Airport Transit System to the Multi-Modal Facility. Weekday trains. Buy tickets from the conductor.	Union Station in downtown Chicago, or north to Antioch.

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 14 fare checks from Boston to Chicago ran from 12 Sep to 15 Oct 2026. For the return direction, Chicago to Boston, EazAir's first 16 checks ran from 13 Sep to 12 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 14 checks returned 11 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

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)
TSA: International checkpoint opens in Logan Terminal E (no date shown, accessed 17 Oct 2026)
Delta: Delta's new O'Hare home (11 Oct 2022, accessed 17 Oct 2026)
O'Hare: Airport Transit System and terminal transfers (no date shown, accessed 17 Oct 2026)
O'Hare: ATS service update (no date shown, accessed 17 Oct 2026)
O'Hare: Public transit (no date shown, accessed 17 Oct 2026)
O'Hare: Taxis and rideshare (no date shown, accessed 17 Oct 2026)
CTA: Airports (no date shown, accessed 17 Oct 2026)
CTA: Fares (fare chart effective 20 Feb 2023, accessed 17 Oct 2026)
Midway: Public transit (no date shown, accessed 17 Oct 2026)
O'Hare: Domestic nonstop destinations (as of 1 Sep 2026, 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 BOS to ORD, 12 Sep 2026 to 15 Oct 2026; ORD to BOS, 13 Sep 2026 to 12 Oct 2026

Frequently asked questions

Does this page search Chicago Midway?

No. It searches O'Hare (ORD). Chicago Midway (MDW) is a separate airport served by the CTA Orange Line, so check which Chicago airport each fare uses before you pay.

Which O'Hare terminal does Delta use?

Delta says it moved its O'Hare flights to Terminal 5 in October 2022. O'Hare's airline list did not load when checked, so travelers on other airlines should use their boarding pass or airline app.

How do I get from O'Hare to downtown Chicago by train?

The CTA Blue Line runs 24 hours from a station on the lower level of the parking garage, and CTA puts the ride downtown at 40 to 45 minutes. Rides starting at O'Hare cost more than a standard CTA fare.

Where is rideshare pickup at O'Hare?

O'Hare lists rideshare pickup on the upper level at Terminal 2, orange poles 2A to 2G, and Terminal 3, green poles 3G to 3K. It lists no Terminal 5 pickup, so check your app.

Which Logan terminal do I leave from?

American lists Terminal B, gates B4 to B22, and JetBlue lists Terminal C. Delta's domestic flights use Terminal A or Terminal E, so check the Fly Delta app or My Trips. United travelers should check their boarding pass.

Do the lowest fares on this route include a carry-on?

Delta, American and JetBlue include a carry-on plus a personal item with their lowest fares. United Basic Economy allows only a personal item on domestic flights unless you are a MileagePlus Premier member, travel with one or hold a qualifying card.

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.