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Cheap flights from Chicago to Boston from £41

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Boston departing on 21/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags
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Wed 15/5
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Easily compare return flights from Chicago to Boston

Below you can see the best fares for your return 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
Delta
30 May
ORD20:10Chicago O'Hare Intl
2h 36m
BOS23:46Boston Logan Intl
4 Jun
BOS06:25Boston Logan Intl
2h 55m
ORD08:20Chicago O'Hare Intl
JetBlue
1 Jun
ORD19:15Chicago O'Hare Intl
2h 26m
BOS22:41Boston Logan Intl
4 Jun
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
Southwest
23 May
ORD11:25Chicago O'Hare Intl
8h 55m
1 stop
BOS21:20Boston Logan Intl
25 May
BOS11:50Boston Logan Intl
5h 35m
1 stop
ORD16:25Chicago O'Hare Intl
United Airlines
24 May
ORD21:45Chicago O'Hare Intl
2h 35m
BOS01:20Boston Logan Intl
28 May
BOS06:00Boston Logan Intl
2h 50m
ORD07:50Chicago O'Hare Intl
Delta
30 May
ORD06:13Chicago O'Hare Intl
2h 27m
BOS09:40Boston Logan Intl
3 Jun
BOS06:25Boston Logan Intl
2h 55m
ORD08:20Chicago O'Hare Intl
JetBlue
25 May
ORD19:15Chicago O'Hare Intl
2h 26m
BOS22:41Boston Logan Intl
29 May
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl

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 Frontier, JetBlue and Spirit Airlines
Frontier
21 May
ORD05:33Chicago O'Hare Intl
5h 24m
1 stop
BOS11:57Boston Logan Intl
Spirit Airlines
21 May
ORD05:00Chicago O'Hare Intl
17h 55m
2 stops
BOS23:55Boston Logan Intl
JetBlue
31 May
ORD19:15Chicago O'Hare Intl
2h 26m
BOS22:41Boston Logan Intl

Search last-minute flights to Boston from Chicago

Find and compare return flight prices for your last-minute flight from Chicago to Boston
Spirit Airlines
8 May
ORD07:00Chicago O'Hare Intl
7h 13m
1 stop
BOS15:13Boston Logan Intl
11 May
BOS22:27Boston Logan Intl
14h 07m
1 stop
ORD11:34Chicago O'Hare Intl
Delta
8 May
ORD06:27Chicago O'Hare Intl
2h 27m
BOS09:54Boston Logan Intl
15 May
BOS06:25Boston Logan Intl
2h 55m
ORD08:20Chicago O'Hare Intl
JetBlue
11 May
ORD08:40Chicago O'Hare Intl
2h 29m
BOS12:09Boston Logan Intl
14 May
BOS16:35Boston Logan Intl
2h 55m
ORD18:30Chicago O'Hare Intl
Delta
10 May
ORD20:10Chicago O'Hare Intl
2h 36m
BOS23:46Boston Logan Intl
12 May
BOS10:15Boston Logan Intl
2h 46m
ORD12:01Chicago O'Hare Intl
Southwest
12 May
ORD07:15Chicago O'Hare Intl
23h 25m
2 stops
BOS07:40Boston Logan Intl
13 May
BOS13:00Boston Logan Intl
10h 20m
1 stop
ORD22:20Chicago O'Hare Intl
JetBlue
10 May
ORD08:40Chicago O'Hare Intl
2h 29m
BOS12:09Boston Logan Intl
11 May
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl

United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets
United Airlines
24 May
ORD21:45Chicago O'Hare Intl
2h 35m
BOS01:20Boston Logan Intl
28 May
BOS06:00Boston Logan Intl
2h 50m
ORD07:50Chicago O'Hare Intl
United Airlines
12 May
ORD07:15Chicago O'Hare Intl
2h 23m
BOS10:38Boston Logan Intl
13 May
BOS09:40Boston Logan Intl
2h 48m
ORD11:28Chicago O'Hare Intl
United Airlines
24 May
ORD21:45Chicago O'Hare Intl
2h 35m
BOS01:20Boston Logan Intl
27 May
BOS05:45Boston Logan Intl
4h 50m
1 stop
ORD09:35Chicago O'Hare Intl

Delta flights from Chicago to Boston

Our best Delta deals on Chicago to Boston flight tickets
Delta
30 May
ORD20:10Chicago O'Hare Intl
2h 36m
BOS23:46Boston Logan Intl
4 Jun
BOS06:25Boston Logan Intl
2h 55m
ORD08:20Chicago O'Hare Intl
Delta
30 May
ORD06:13Chicago O'Hare Intl
2h 27m
BOS09:40Boston Logan Intl
3 Jun
BOS06:25Boston Logan Intl
2h 55m
ORD08:20Chicago O'Hare Intl
Delta
1 Jun
ORD17:15Chicago O'Hare Intl
2h 29m
BOS20:44Boston Logan Intl
20 Aug
BOS14:40Boston Logan Intl
2h 52m
ORD16:32Chicago O'Hare Intl

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. The most expensive is June.

What is the cheapest day to depart Chicago for Boston?

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

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

In the morning. Chicago to Boston flights are approximately 53% more expensive in the afternoon than in the morning

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?

32 days before. The cheapest time to buy a flight from Chicago to Boston is approximately 32 days to departure

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

As of May 2024, 57 flights take off from Chicago and land in Boston each day. The most common flight departure time for this route is 12:00, with 54% of daily flights taking off in the afternoon.

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

401 flights are operational weekly from Chicago to Boston as of May 2024. The most popular departure day for this route is Monday, with 16% of flights per week taking off on this day.

Can stopping save me money on Chicago to Boston flights?

You could potentially save up to 13% on your flight if you consider stops on a Chicago to Boston flight.

Cheap Chicago to Boston (CHI to BOS) flight deals and tips

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

Best price found

£41

Fastest flight time

2h 22m

Direct flights

Every day

Airports in Boston

1 airport
The best one-way flight to Boston from Chicago in the past 72 hours is £41. The best return flight deal from Chicago to Boston found on momondo in the last 72 hours is £109.
The fastest flight from Chicago to Boston takes 2h 22m
Direct flights go from Chicago to Boston every day.
There is 1 airport near Boston: Boston Logan Intl (BOS)

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

    The quickest way to travel this route is to take a flight from Chicago to Boston, doing so can potentially save up to 24h 53m of travel time. While these options may take longer, booking a train from Chicago to Boston or a bus from Chicago to Boston may suit your needs if travel time is less of a factor in your decision making.

  • 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 £156, or consider a bus from Chicago to Boston starting at £186. Both of these alternative options are worth considering when looking to reach your destination.

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

    Chicago and Boston Logan Intl are 847.9 mi apart from one another. Flights usually cover this in 2h 22m, depending on flying conditions and air traffic around both airports.

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

    830lb is the expected carbon footprint of a flight from Chicago to Boston Logan Intl, though you can sort and filter momondo flight search results by CO2 to find the best option. By train, you could lower your emissions for this trip by about 78%. Emissions for travelling this route by bus are generally around 119lb.

  • 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 were last updated today.

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, 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.


Why use momondo?

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

Finding the right flight to Boston from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Boston quick and easy, saving you time and money.

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

momondo does allow users to show only those flights to Boston from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Boston.

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

If you are simply researching potential flights to Boston, momondo offers a useful price alert feature which will track prices for flights to Boston from Chicago and alert you when they change.


Choose the best way to get from Chicago to Boston

Buses

27h 00m
£69 one-way£186 return
Direct · from £186

Distance to city centre

ZTO0.6 mi
4O43.4 mi
119lb CO2

86% less than flights

Find Buses

Chicago to Boston Buses

Trains

21h 54m
£78 one-way£156 return
Direct · from £156

Distance to city centre

ZTO0.6 mi
ZTY1.3 mi
189lb CO2

77% less than flights

Find Trains

Chicago to Boston Trains

Flights

2h 22m
£41 one-way£109 return
Direct · from £1091 stop · from £44

Distance to city centre

BOS2.6 mi

An easier way to manage your Boston trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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