$116 Find Cheap Flights from Boston to Illinois - Compare and Save

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Cheap Flights from Boston to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Chicago
Chicago1 stop$216
Moline
Moline1 stop$359
Peoria
Peoria1 stop$359
Bloomington
Bloomington1 stop$376
Champaign
Champaign1 stop$490
Springfield
Springfield1 stop$573
Decatur
Decatur1 stop$384
Paducah
Paducah1 stop$474
Chicago
Chicago1 stop$216
Moline
Moline1 stop$359
Peoria
Peoria1 stop$359
Bloomington
Bloomington1 stop$376
Champaign
Champaign1 stop$490
Springfield
Springfield1 stop$573
Decatur
Decatur1 stop$384
Paducah
Paducah1 stop$474
Booking Insights

Price, demand and travel trends for Boston to Illinois flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Boston to Illinois recently?

The cheapest fares from Boston to Illinois on KAYAK in the last week were to Chicago O'Hare Intl (ORD) from $216 round-trip and to Chicago Midway (MDW) from $245 round-trip.

How do fares into airports in Illinois compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Illinois from Boston are:

• Chicago O'Hare Intl (ORD) (avg. price $256)
• Chicago Midway (MDW) (avg. price $277)
• Moline Quad-City (MLI) (avg. price $418)

Are flights from Boston to Illinois cheaper or more expensive than last year?

Fares from Boston to Illinois are about 10% higher than they were in November last year, averaging $295 round-trip.

What's the cheapest month to fly from Boston to Illinois?

January is typically the cheapest month to fly from Boston to Illinois, with round-trip fares averaging $188. October and November are usually the most expensive, averaging $345 and $321, respectively.

How do fares from Boston to Illinois vary by day of the week?

On average, Saturday is the cheapest day to fly from Boston to Illinois and Friday is the most expensive. Looking at the past 12 months of KAYAK data, it's 15% more expensive to fly on a Friday compared to Saturday.

What's the best time of day to fly from Boston to Illinois?

It's cheapest to fly to Illinois in the morning with average prices of $257. The night is the most expensive time to fly, with average prices of $358.

What's the best time to book a flight from Boston to Illinois?

Book your flights 6 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 23% compared to booking at the last minute (within 2 weeks of departure).

Key details for Boston to Illinois flights

Low season

February

Cheapest flight

$116
Beat the crowds with an average 25% drop in travelers.
The most popular month to fly with an average 30% increase in travelers.
One-way flight from Boston to Chicago O'Hare Intl Airport

Flights from Boston to Illinois: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Boston to Illinois 
WeiFlew with United Airlines-Oct 2026
This flight usually departs from gate B28. Enjoy a quick meal at Legal’s or Stephanie’s, refill your water bottle at the water station nearby, and enjoy the very quick boarding process implemented!
GailFlew with JetBlue-Jul 2024
Prepare for a long wait after you actually touch down. Ohare Airport is HUGE and you can taxi for a long time.

Your Boston to Illinois flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Boston to Illinois?

    Fares from Boston to Illinois are around their usual level right now. A round-trip under $203 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch fare changes.

  • How much should I budget for a flight from Boston to Illinois?

    Over the past 12 months, round-trip fares from Boston to Illinois have typically cost between $203 and $349.

  • What are the main airports serving Illinois?

    There are 17 airports in Illinois. 85% of KAYAK users choose Chicago O'Hare Intl (ORD) as their arrival airport, while 13% choose Chicago Midway (MDW).

  • Which airlines fly nonstop from Boston to Illinois?

    Based on the flight schedule for the next 3 months, 5 airlines offer nonstop flights on this route:

    • American Airlines
    • United Airlines
    • Delta
    • Southwest
    • JetBlue

  • Which destinations in Illinois can I fly nonstop from Boston?

    Based on the flight schedule for the next 3 months, you can fly nonstop from Boston to just one destination in Illinois: Chicago.

  • Is it cheaper to fly with a layover from Boston to Illinois?

    Yes, nonstop flights from Boston to Illinois average $259 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Orlando (MCO) (avg. price $157)
    • Baltimore/Washington (BWI) (avg. price $182)
    • New York John F Kennedy Intl (JFK) (avg. price $187)

  • How long is a flight from Boston to Illinois?

    Nonstop flights from Boston to Illinois take 3h 07m on average. The fastest scheduled flight takes 2h 40m, flying into Chicago Midway (MDW).

  • Which cabin classes are available from Boston to Illinois?

    On flights from Boston to Illinois you can book Economy Class, Premium Economy Class, Business Class or First Class.

  • What are some popular landmarks around Illinois?

    Illinois is home to many popular sights. KAYAK travelers' favorites include:

    • Magnificent Mile
    • Grant Park
    • Soldier Field
    • River North

  • What are the earliest and latest flights from Boston to Illinois?

    The earliest nonstop flight from Boston to Illinois departs at 5:00 am and the latest leaves at 10:25 pm. Nonstop flights take about 3h 07m.

Your guide to booking Boston to Illinois flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 6 weeks before your trip. KAYAK data shows fares in this window are around 23% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in January to save some money. It's typically the cheapest month on this route, while flights in October will cost you the most.
  • Fly out on a Saturday to get the cheapest fares. Avoid Friday flights, which are about 15% more expensive.
  • If you're watching your budget, fly into Chicago O'Hare Intl (ORD) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Chicago, the most popular destination in Illinois. From there, it's easy to continue on to other popular spots such as Rosemont, Schaumburg and Champaign.
  • Time or money? If speed matters most, fly from Boston to Chicago Midway (MDW). If you're after the lowest fares, Chicago O'Hare Intl (ORD) is usually your best bet.

Reviews of the top 5 airlines serving from Boston to Illinois

 
Need help choosing which airline to fly with from Boston to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4222 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

Crew was a little surly. But plane left on time and arrived early. All one can ask for. New 737 Max was nice.

10.0 ExcellentChad, Nov 2026
Read more Southwest reviews

Crew was a little surly. But plane left on time and arrived early. All one can ask for. New 737 Max was nice.

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

It was the strangest thing. The flight attendant (who was not very friendly) took our drink orders and then never brought them. I’ve never had that happen before.

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

WiFi was not working and didn’t have a beverage service

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

Travelling with 2 others for work. Delta asked to check their carry ons due to the fullness of the plane. This was all good until the next leg of the flight. One of the 3 had their carry on checked through to the final destination but their passport on in their checked bag. Which they could not get to and he was not allowed on to the plane. Even though Delta had to retrieve his bag, because he was not allowed on. So they got his bag and he was in the terminal, but even when the flight was delayed, due to mechanical issues, he was not allowed to come onto the plane. Since the delay was nearly 2 hours, he was finally allowed back on the plane.

Boarding was delayed by an hour and then we proceeded to sit on the tarmac for another 30-40 minutes. No clear explanation was ever given and the delay caused me to miss my connecting flight home. Was forced to stay the night in the connecting city which impacted my following workday and cause personal issues at home as well.

Good flight — left on time due to on time arrival of Pittsburgh flight

Delta keep on impressing me. Right now Delta airline is the best of them all

Good but since we got in early we had to wait on runway for our gate. That was kind of a bummer but we still got in earlier than planned For entertainment I was watching a movie and getting close to the end of it with 15 min left but it kept jumping automatically to the next movie before finishing.

13 hour delay stuck in Detroit and missed a day of meetings. It was terrible

Great crew. Comfortable seating. Nice overhead bin space. My app didn't allow me to check in for my flight to BOS. When I called Support, they didn't fix it, but just told me to check in at the airport. Seat back entertainment was great. Could be better if the audio could connect to Bluetooth.

The cabin was definitely dated, but that's about par for the course. The flight crew were wonderful as always (always a Delta highlight), but the boarding process was slow with little direction or encouragement to get people in their seats quickly since we were already delayed.

Totally organized, quick boarding, professional staff and ON TIME! Good size seats in the cabin Wonderful experience

The flight was delayed to board, then delay in landing and extremely bumpy landing.

⭐ Absolutely AWFUL Experience with United Airlines! If I could give United Airlines ZERO stars, I would. The seats have practically NO legroom, making the flight feel like being crammed into a tin can with nowhere to move. Comfort? Forget about it! And the fees? Absolutely ridiculous! They seem to charge you for EVERYTHING. You pay for your ticket, then get hit with extra charges for things that should be part of a decent flying experience. What’s next, charging passengers for breathing? Flying with United feels less like being a valued customer and more like being a walking wallet. The seats are uncomfortable, the legroom is pathetic, and the constant nickel-and-diming is infuriating. For the price you pay, you would think they could at least provide a little space to stretch your legs and a travel experience that doesn’t leave you feeling ripped off. Do yourself a favor and look at other airlines before booking with United. I certainly won’t be rushing to fly with them again. Absolutely disappointing from start to finish!

Flight was very smooth from Boston. But when we got to Houston, the gate was not open and we waited on the runway for over 30 min!!

My flight from Boston to SFO was fine. Crew was friendly and helpful. Food was mediocre. Fright from SFO to MNL was not as good. My flight attendant was friendly but didn’t seem to have a lot of experience. She seemed overwhelmed. Also, this was the only red eye business class flight I’ve flown which only served dinner 2 hours after takeoff in a 13 hr flight. When I woke up 1 hr before landing, everyone was eating so I assumed bkft was being served. I pushed my button for help and no one came so I approached my flight attendant and she said they don’t serve bkft but she gave me choices for lunch or dinner. I routinely fly business class but I was disappointed with the lack of service and attention I was given on this flight. Also, most airlines will offer a snack or coffee before bkft is served but this was not offered during this flight. Overall, it was disappointing.

Horrible on the chicago end. They change hates then there is a plane at the new gate so we can’t pull in. Then that plane has mechanical issue and needs to be pulled back to the gate but we can’t get to another new gate due the other plane being in the way. Horrible gate management which will cause many customers to miss connections.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

Great, except the canon was so cold. Even the flight attendants put jackets on

The app logs you out right when you are boarding requiring all passwords and reservation number for the flight. Super annoying

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

1/2 full flight, nice and comfy flight. On time, good service

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

Left a bit late duee to a technical issue, but got in early

Wonderful aircraft Crew was tired,but great considering On time No complaints

Your Jet Blue representative at the check in desk in Boston on Sunday morning, October 13, was unkind and unhelpful. For that reason alone I will avoid JetBlue airlines in the future. No food or beverage on the flight due to turbulence (not your fault). However I paid extra to sit in the upgraded section in the front and did not benefit from most amenities.

Multiple delays, poor communication, dismissive staff, chaotic boarding, broken seat back entertainment. Not really much to like.

There was more leg room in what was most likely a basic assigned seat (row 25) then on other airlines I've flown lately.

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

Boston sucks. Everything after 4p is delayed. AA switched planes on us so we ended up being 1.5 hours late (plus the delay at Logan). Not sure why the airline says it is on time until 1 h before the flight and then it becomes a rolling delay when they knew the incoming flight was arriving after our scheduled departure time. The crew was great as were the gate agent and ground crew. Just operations that sucked.

Flight was 2 hr late but at least I was upgraded to first class

I've flown American several times this summer and I have yet to get a flight that leaves on time. However, a delay is better than a cancel. So far I have had four canceled flights and two delayed flights

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

They have overselled the ticket and kicked me out from boarding, All my Plans were collapsed and important network meeting missed.also I booked direct flight i have to go through an 1 stop and it was frustrated.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

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.

Despite a bumpy flight the pilot was great. The rest of the crew on the other hand couldn’t care less if a passenger would colapse and die. Horrible service, robot like, lifeless…

More options for your flight from Boston to Illinois

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