Economy Plus offers 6 inches more legroom than standard economy seats, enhancing comfort.
Priority Boarding places you in Zone 2, ensuring overhead bin space for your carry-on.

Planning a trip from Chicago to Boston? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.
When planning a flight from Chicago to Boston, there are several strategies to consider for saving money. Generally, the cheapest day of the week to fly is Wednesday, and the most affordable month is September.
Booking Advance: Purchase tickets at least 90 days in advance for the best rates.
Airline Choice: Consider flying with Frontier, as it is generally the cheapest airline for this route.
Route Selection: Flights from Chicago Midway (MDW) to Boston Logan (BOS) tend to be the most affordable.
Direct or Layover: Direct flights are significantly more expensive, so consider flights with layovers to save money.
AI-powered; AI can make mistakes.
| Low season | January |
|---|---|
| High season | June |
| Cheapest flight | $64 |
Direct departures
Chicago to Boston Logan Intl
Monday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Tuesday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Wednesday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Thursday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Friday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Saturday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Sunday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Direct returns
Boston Logan Intl to Chicago
Monday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Tuesday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Wednesday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Thursday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Friday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Saturday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Sunday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
3 hour delay. Had to change plans and was still delayed.
3 hour delay. Had to change plans and was still delayed.
The staff was very friendly, professional, and courteous. The overall flight was a great experience.
The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.
Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.
We got exit row seats both flights. Everything was running on time
The flight crew was extremely rude and especially not helpful when our flight was delayed.
Pretty seamless, just a tad bit late in taking off and landing.
Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.
Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.
Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.
Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.
Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.
It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.
Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.
Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.
I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.
Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.
DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.
Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.
This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.
I like flying first class, and United has a nice one
They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!
I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...
cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.
Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/
Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.
United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent
I liked the snacks and the flight attendants were friendly.
After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.
Very thoughtful flight attendant offered me water immediately since I had run to make my connection.
We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.
My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!
Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.
The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.
The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.
We loved the steward on the plane. He made the night enjoyable
The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.
They only offered water for Group 6. Awful announcements from the Crew. Couldn't understand a single word. Barely came by for the trash afterwards. Man, I love water for a premium flight. Wow. Water in a cup.
Ring in first class for an overnight flight, there was no blankets nor pillows for first class customers.
Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.
Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.
First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.
1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready
It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.
we were delayed because of some safety check that wasn't done or available
The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.
The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.
Very pleasant flight attendants. Gate crew rather loud chatting with each other.
Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.
Friendly crew. Poor food service maybe due to full flight. All in all, you get what you pay for.
| Transportation mode | Average price | Average duration |
|---|---|---|
| Flights | $675 | 2h 10m |
| Trains | $300 | 21h 57m |