Cheap flights from Chicago to Boston from $42

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Flight information for Chicago to Boston
(CHI to BOS)

Find info about flight duration, direct flights, and airports for your flight from Chicago to Boston

Best Price Found

$42

Fastest flight time

2h 05m

Direct flights

Every day

Airports in Boston

1 airport
The best one-way flight to Boston from Chicago in the past 72 hours is $42. The best round-trip flight deal from Chicago to Boston found on momondo in the last 72 hours is $85.
The fastest flight from Chicago to Boston takes 2h 05m
Direct flights go from Chicago to Boston every day.
There is 1 airport near Boston: Boston Logan Intl (BOS)

How to get the cheapest flight ticket from Chicago to Boston

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Chicago to Boston?

February. The cheapest time of year to fly to Boston from Chicago is February. Most expensive is June

What is the cheapest day to depart Chicago for Boston?

Saturday. The cheapest day of the week is typically Saturday. The most expensive is typically Monday

When is the cheapest time to fly from Chicago to Boston?

In the evening. Chicago to Boston flights are approximately 21% more expensive in the afternoon than in the evening

What is the cheapest airline that flies to Boston from Chicago?

Spirit Airlines. American Airlines, Delta, and JetBlue are the most popular carriers operating from Chicago to Boston

What is the cheapest Chicago to Boston flight route?

Chicago O'Hare Intl - Boston Logan Intl. Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago - Boston flight prices

How far in advance should you book Chicago to Boston flights?

9 days before. The cheapest time to buy a flight from Chicago to Boston is approximately 9 days to departure

How many flights depart from Chicago to Boston on average per day?

As of September 2023, there are 57 flights per week flying from Chicago to Boston. The most common time of day flights depart is 12:00PM, with 49% of flights taking off in the afternoon.

How many flights depart from Chicago to Boston on average per week?

As of September 2023, 401 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Monday, with 16% of weekly flights taking off on this day.

What cabin class options are available on Chicago to Boston flights?

There are 4 cabin classes available to choose from on Chicago to Boston flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Boston flights?

You could potentially save up to 17% on your flight if you consider stops on a Chicago to Boston flight.

When traveling from Chicago to Boston, the most popular airport to fly into is Boston Logan Intl Airport. The majority of travelers flying into Boston Logan Intl Airport from Chicago are departing from Chicago O'Hare Intl Airport. When booking your trip to Boston, it is helpful to have an alternative airport to fly out of. The nearest airport to Chicago O'Hare Intl Airport is Chicago Midway Airport which is located in Chicago. When traveling from Chicago, it is helpful to have an alternative airport to fly into when you land in Boston. The nearest airport to Boston Logan Intl Airport is Manchester Airport which is located in Manchester. In September, $98 is typically the cheapest round trip price you’ll find from Chicago to Boston which you can find when you fly ORD — BOS.

Chicago O'Hare Intl Airport (ORD) to Boston Logan Intl Airport (BOS)$98
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Chicago Midway Airport (MDW) to Boston Logan Intl Airport (BOS)$116
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Chicago O'Hare Intl Airport (ORD) to Manchester Airport (MHT)$172
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Chicago Midway Airport (MDW) to Manchester Airport (MHT)$169
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Easily compare round-trip flights from Chicago to Boston

Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Boston by changing tabs
Frontier
Oct 10
MDW3:29 amChicago Midway
24h 01m
1 stop
BOS3:30 amBoston Logan Intl
Oct 17
BOS8:09 amBoston Logan Intl
5h 05m
1 stop
MDW1:14 pmChicago Midway
JetBlue
Oct 28
ORD4:30 pmChicago O'Hare Intl
2h 24m
BOS6:54 pmBoston Logan Intl
Oct 31
BOS3:05 amBoston Logan Intl
3h 00m
ORD6:05 amChicago O'Hare Intl
Spirit Airlines
Oct 17
ORD7:50 amChicago O'Hare Intl
11h 09m
1 stop
BOS6:59 pmBoston Logan Intl
Oct 18
BOS12:50 pmBoston Logan Intl
16h 34m
1 stop
ORD5:24 amChicago O'Hare Intl
Multiple Airlines
Oct 21
ORD6:24 amChicago O'Hare Intl
9h 26m
1 stop
BOS3:50 pmBoston Logan Intl
Nov 4
BOS12:55 pmBoston Logan Intl
3h 01m
ORD3:56 pmChicago O'Hare Intl
Delta
Oct 25
ORD2:10 amChicago O'Hare Intl
2h 23m
BOS4:33 amBoston Logan Intl
Oct 28
BOS1:40 pmBoston Logan Intl
2h 59m
ORD4:39 pmChicago O'Hare Intl
Frontier
Oct 28
MDW1:17 pmChicago Midway
14h 33m
1 stop
BOS3:50 amBoston Logan Intl
Oct 30
BOS8:09 amBoston Logan Intl
8h 49m
1 stop
MDW4:58 pmChicago Midway

Find the cheapest one-way flights from Chicago to Boston

If you're looking for one-way flights from Chicago to Boston, view some of our deals below provided by American Airlines, Frontier and JetBlue
Frontier
Oct 10
MDW1:06 pmChicago Midway
17h 22m
1 stop
BOS6:28 amBoston Logan Intl
JetBlue
Oct 17
ORD4:30 pmChicago O'Hare Intl
2h 24m
BOS6:54 pmBoston Logan Intl
Spirit Airlines
Oct 11
ORD7:50 amChicago O'Hare Intl
11h 09m
1 stop
BOS6:59 pmBoston Logan Intl

Search last-minute flights to Boston from Chicago

Find and compare round-trip flight prices for your last-minute flight from Chicago to Boston
Frontier
Sep 27
MDW6:17 amChicago Midway
21h 15m
1 stop
BOS3:32 amBoston Logan Intl
Sep 30
BOS8:59 amBoston Logan Intl
6h 25m
1 stop
MDW3:24 pmChicago Midway
Spirit Airlines
Sep 27
ORD4:00 amChicago O'Hare Intl
10h 37m
1 stop
BOS2:37 pmBoston Logan Intl
Oct 3
BOS4:32 pmBoston Logan Intl
17h 42m
2 stops
ORD10:14 amChicago O'Hare Intl
Multiple Airlines
Sep 26
ORD3:54 pmChicago O'Hare Intl
15h 25m
2 stops
BOS7:19 amBoston Logan Intl
Oct 10
BOS7:25 amBoston Logan Intl
11h 48m
1 stop
ORD7:13 pmChicago O'Hare Intl
JetBlue
Sep 26
ORD4:30 pmChicago O'Hare Intl
2h 24m
BOS6:54 pmBoston Logan Intl
Sep 30
BOS1:35 pmBoston Logan Intl
2h 59m
ORD4:34 pmChicago O'Hare Intl
American Airlines
Sep 30
ORD4:22 pmChicago O'Hare Intl
2h 22m
BOS6:44 pmBoston Logan Intl
Oct 4
BOS1:35 amBoston Logan Intl
2h 54m
ORD4:29 amChicago O'Hare Intl
United Airlines
Sep 26
ORD8:45 amChicago O'Hare Intl
2h 21m
BOS11:06 amBoston Logan Intl
Sep 28
BOS2:00 amBoston Logan Intl
2h 52m
ORD4:52 amChicago O'Hare Intl

Best airlines flying from Chicago to Boston

Compare and see reviews for airlines that fly from Chicago to Boston with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $79Free CancellationRating
6.9
1,103 reviews
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DeltaPriceFrom $79Free CancellationRating
7.8
1,565 reviews
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Alaska AirlinesPriceFrom $80Free CancellationRating
7.9
2,995 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $84Free CancellationRating
7.2
2,711 reviews
Search United Airlines flights
American AirlinesPriceFrom $108Free CancellationRating
7.1
2,886 reviews
Search American Airlines flights
Spirit AirlinesPriceFrom $117Free CancellationRating
6.0
2,808 reviews
Search Spirit Airlines flights
  • Alaska Airlines Flights From Chicago to Boston

    Alaska Airlines flight deals from Chicago to Boston start from $80 round-trip. Over the 27 Alaska Airlines flights for this route in a normal week, average airfare is usually $337 round-trip - but some users have found much cheaper deals with momondo.

  • Delta Flights From Chicago to Boston

    Another popular option for Chicago to Boston flights is Delta (7.8/10, 1,565 ratings). Delta flies from Chicago to Boston around 29 times per week, with deals starting from $79 round-trip and rising to an average price of around $302.


Frontier flights from Chicago to Boston

Our best Frontier deals on Chicago to Boston flight tickets
Frontier
Oct 10
MDW3:29 amChicago Midway
24h 01m
1 stop
BOS3:30 amBoston Logan Intl
Oct 17
BOS8:09 amBoston Logan Intl
5h 05m
1 stop
MDW1:14 pmChicago Midway
Frontier
Oct 28
MDW1:17 pmChicago Midway
14h 33m
1 stop
BOS3:50 amBoston Logan Intl
Oct 30
BOS8:09 amBoston Logan Intl
8h 49m
1 stop
MDW4:58 pmChicago Midway
Frontier
Nov 4
MDW4:06 pmChicago Midway
11h 21m
1 stop
BOS2:27 amBoston Logan Intl
Nov 13
BOS7:09 amBoston Logan Intl
8h 49m
1 stop
MDW3:58 pmChicago Midway

United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets
United Airlines
Oct 29
ORD3:10 amChicago O'Hare Intl
2h 19m
BOS5:29 amBoston Logan Intl
Nov 4
BOS2:28 pmBoston Logan Intl
2h 57m
ORD5:25 pmChicago O'Hare Intl
United Airlines
Oct 1
ORD3:37 amChicago O'Hare Intl
2h 21m
BOS5:58 amBoston Logan Intl
Oct 4
BOS1:45 amBoston Logan Intl
4h 43m
1 stop
ORD6:28 amChicago O'Hare Intl
United Airlines
Oct 13
ORD5:18 pmChicago O'Hare Intl
2h 27m
BOS7:45 pmBoston Logan Intl
Oct 17
BOS2:00 amBoston Logan Intl
5h 44m
1 stop
ORD7:44 amChicago O'Hare Intl

Choose the best way to get from Chicago to Boston


  • Is flying the fastest way to get from Chicago to Boston?

    The quickest way is to book a flight from Chicago to Boston, which can be as quick as 2h 05m onboard Southwest. You can also get a train from Chicago to Boston, or a bus from Chicago to Boston which can take you longer to arrive at your destination.

  • Is flying the cheapest way to get from Chicago to Boston?

    A flight from Chicago to Boston is currently going to be the least expensive option currently available. You can also find deals for a train from Chicago to Boston starting at $194, or consider a bus from Chicago to Boston starting at $315. Both of these alternative options are worth considering when looking to reach your destination.

  • How far is Chicago to Boston Logan Intl by plane?

    The distance between Chicago and Boston Logan Intl is about 847.9 mi. 2h 05m is a normal flight duration for this route.

  • What is the carbon footprint of flying from Chicago to Boston Logan Intl?

    Flying from Chicago to Boston Logan Intl has a carbon footprint of about 666lb. Flight search results on momondo can be sorted by their carbon footprint. The carbon footprint of this journey by train would be 188lb - a 72% reduction. By bus, this journey’s emissions can be cut to 119lb. This would result in a 83% smaller carbon footprint vs. flying.

  • When did momondo last update prices for flights from Chicago to Boston Logan Intl Airport?

    Prices for flights from Chicago to Boston Logan Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago to Boston Logan Intl Airport?

  • How old do you have to be to fly from Chicago to Boston Logan Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Boston Logan Intl Airport.

  • What documentation or ID do you need to fly to Boston Logan Intl Airport?

    The travel and health documents you'll need for your trip to Boston Logan Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Boston Logan Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.


Alternative routes for Chicago to Boston

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
St. Louis to Boston Flights
Fastest flight time2h 29m
Cheapest price$135
Chicago to Nantucket Flights
Fastest flight time3h 55m
Cheapest price$348
Chicago to Provincetown Flights
Fastest flight time5h 40m
Cheapest price$484

Similar Chicago to Boston flights

Flexible with your destination? Broaden your search and find flights similar to your Chicago to Boston route

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Boston?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Boston. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Boston with flexible booking policies on momondo?

All flight searches from Chicago to Boston on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Boston?

momondo provides multiple filters to help you find the best flight to Boston from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Boston right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Boston flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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