American's Main Cabin Extra offers early boarding and complimentary drinks for a fee.
American Airlines provides high-speed Wi-Fi for purchase on most flights, enhancing connectivity.

Planning a trip from Boston to Chicago? 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 Boston to Chicago, it's important to consider a few factors to ensure you're getting the best deal. Generally, Tuesdays are the cheapest day of the week to fly, while January tends to be the cheapest month.
Day Selection: Choose to fly on a Tuesday for the best rates.
Advance Booking: Book your flight at least 23 days in advance to secure the best prices.
Airline Choice: Spirit Airlines typically offers the cheapest fares for this route.
Route Selection: The route from Boston Logan Intl to Chicago O'Hare Intl is usually the cheapest.
Flight Type: Direct flights are significantly more expensive, consider flights with layovers to save money.
AI-powered; AI can make mistakes.
| Low season | January |
|---|---|
| High season | May |
| Cheapest flight | $62 |
Direct departures
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
Direct returns
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
Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!
Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!
No delays and arrived to destination 30 min early. Staff was super friendly.
San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.
It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.
Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight
Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.
Everything a cheap airline should be at normal airline rates.
Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.
Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.
Full cans of soda would be nice. A choice between two snacks would be appreciated.
I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!
Good seats in Main cabin, excellent service and excellent landing
My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.
Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗
Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!
No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.
We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.
First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!
This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.
It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.
Very bad! They kept delaying my flight and wouldn’t do anything about it
They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.
Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.
Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.
Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.
After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.
Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.
Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍
Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.
Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!
I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable
It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.
It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.
After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.
Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.
This was the best 2 flights I have had with American out of SGF. Great crew both flights.
Excellent - explanations were clear staff was nice and flight was comfortable
Lost bag and 2 days no word leaving for cruise no clothes or stuff
Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.
Food was ok, but not as good as I have had before on AA.
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.
Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!
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.
Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.
Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.
I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).
They have the most inexperienced / rude flight staff I’ve encountered
very difficult boarding process - aggressive passengers not the friendliest crew
| Transportation mode | Average price | Average duration |
|---|---|---|
| Flights | $634 | 2h 45m |
| Trains | $349 | 22h 21m |