How far in advance should I book tickets for a flight with Spirit Airlines from Boston to Chicago?

Generally, when trying to get a below average price for your ticket, try to book around 7 days before departure. For the cheapest possible price, our data suggests booking 91 days before departure.

Is Spirit Airlines the cheapest airline to fly with from Boston to Chicago?

Yes, based on our data, Spirit Airlines is the cheapest airline to fly the route with an average price of $104 return. The next cheapest options are Frontier and JetBlue, with return flights costing on average $151 and $217 respectively.

What is the cheapest Spirit Airlines flight from Boston to Chicago?

In the last 3 days, the lowest price for a flight with Spirit Airlines from Boston to Chicago was $97 for a return flight and $48 for a one-way flight.

Does Spirit Airlines fly direct to Chicago from Boston?

No, Spirit Airlines does not fly the route directly.

What’s the cheapest day of the week to fly from Boston to Chicago with Spirit Airlines?

On average, the cheapest day of the week to fly from Boston to Chicago with Spirit Airlines is Monday, when prices are around $20. The most expensive day is generally Sunday, where the average price is around $39.

What’s the cheapest month to fly from Boston to Chicago with Spirit Airlines?

The cheapest month for Spirit Airlines flights to Chicago from Boston is generally September, where plane tickets cost $42 on average. If possible, try to avoid the most expensive months of April and December, where tickets cost $131 and $214 respectively.

$45 Cheap Spirit Airlines Flights from Boston to Chicago

Flights Deals

Cheap Spirit Airlines Flight Deals from Boston to Chicago

Here are some of the best deals found on KAYAK recently from Spirit Airlines for round-trip flights from Boston to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Round-trip

One-way

Last minute

Direct

Recent round-trip Spirit Airlines flight deals from Boston to Chicago

KAYAK's recommended round-trip Spirit Airlines deals departing in the coming months from Boston to Chicago.

Discover the best prices for you by selecting your travel dates on KAYAK.

8:00 am - 9:53 amBOS-ORD

2h 53mnonstop

3:29 pm - 12:39 amORD-BOS

8h 10m1 stop

$113Spirit Airlines

Find Deal

Thu, Oct 23 - Tue, Oct 28

3:49 pm - 11:04 pmBOS-ORD

8h 15m1 stop

7:37 am - 9:50 pmORD-BOS

13h 13m1 stop

$118Spirit Airlines

Find Deal

Wed, May 28 - Wed, Jun 4

3:49 pm - 11:04 pmBOS-ORD

8h 15m1 stop

5:05 am - 2:44 pmORD-BOS

8h 39m1 stop

$120Spirit Airlines

Find Deal

Wed, Jun 4 - Wed, Jun 11

3:49 pm - 11:04 pmBOS-ORD

8h 15m1 stop

12:41 pm - 11:29 pmORD-BOS

9h 48m1 stop

$124Spirit Airlines

Find Deal

Wed, Jun 4 - Wed, Jun 11

3:49 pm - 11:04 pmBOS-ORD

8h 15m1 stop

5:05 am - 2:44 pmORD-BOS

8h 39m1 stop

$129Spirit Airlines

Find Deal

Wed, May 28 - Mon, Jun 2

3:49 pm - 11:04 pmBOS-ORD

8h 15m1 stop

12:41 pm - 11:29 pmORD-BOS

9h 48m1 stop

$131Spirit Airlines

Find Deal

Wed, May 28 - Tue, Jun 3

3:49 pm - 11:04 pmBOS-ORD

8h 15m1 stop

5:05 am - 2:44 pmORD-BOS

8h 39m1 stop

$132Spirit Airlines

Find Deal

Wed, May 28 - Mon, Jun 2

3:49 pm - 11:04 pmBOS-ORD

8h 15m1 stop

12:41 pm - 11:29 pmORD-BOS

9h 48m1 stop

$135Spirit Airlines

Find Deal

Tue, Jun 3 - Sat, Jun 7

10:30 am - 4:25 pmBOS-ORD

6h 55m1 stop

7:37 am - 9:50 pmORD-BOS

13h 13m1 stop

$139Spirit Airlines

Find Deal

Mon, May 19 - Wed, Jun 4

3:49 pm - 11:04 pmBOS-ORD

8h 15m1 stop

9:55 am - 11:29 pmORD-BOS

12h 34m1 stop

$140Spirit Airlines

Find Deal

Wed, May 28 - Sun, Jun 1

Useful Info

Low season	January
High season	May
Cheapest flight	$45
Average price round-trip	$275

Best time to beat the crowds with an average 19% drop in price.

Most popular time to fly with an average 15% increase in price.

Flight from Boston to Chicago O'Hare Airport

(price for this month)

When to Book Flights with Spirit Airlines from Boston to Chicago

Average price per month

Flight prices as travel date approaches

How far in advance should I book tickets for a flight with Spirit Airlines from Boston to Chicago?
Generally, when trying to get a below average price for your ticket, try to book around 7 days before departure. For the cheapest possible price, our data suggests booking 91 days before departure.
Is Spirit Airlines the cheapest airline to fly with from Boston to Chicago?
Yes, based on our data, Spirit Airlines is the cheapest airline to fly the route with an average price of $104 return. The next cheapest options are Frontier and JetBlue, with return flights costing on average $151 and $217 respectively.
What is the cheapest Spirit Airlines flight from Boston to Chicago?
In the last 3 days, the lowest price for a flight with Spirit Airlines from Boston to Chicago was $97 for a return flight and $48 for a one-way flight.
Does Spirit Airlines fly direct to Chicago from Boston?
No, Spirit Airlines does not fly the route directly.
What’s the cheapest day of the week to fly from Boston to Chicago with Spirit Airlines?
On average, the cheapest day of the week to fly from Boston to Chicago with Spirit Airlines is Monday, when prices are around $20. The most expensive day is generally Sunday, where the average price is around $39.
What’s the cheapest month to fly from Boston to Chicago with Spirit Airlines?
The cheapest month for Spirit Airlines flights to Chicago from Boston is generally September, where plane tickets cost $42 on average. If possible, try to avoid the most expensive months of April and December, where tickets cost $131 and $214 respectively.

6.3

OkayBased on 7,963 verified guest reviews

6.6Boarding

5.1Food

5.0Entertainment

7.1Crew

5.9Comfort

Pros +

Cons -

Show reviews that mention

4.0 Mediocre

Lauren, Apr 2025

LAX-ORD

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

2.0 Poor

Jane, Apr 2025

TPA-ORD

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

8.0 Very good

Jose, Apr 2025

DFW-LGA

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

10.0 Wonderful

Maya, Apr 2025

DFW-EWR

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

2.0 Poor

Vienna, Apr 2025

BNA-EWR

Delayed a ton of time

4.0 Mediocre

Verified traveler, Apr 2025

MYR-ROC

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

10.0 Wonderful

Alexis, Apr 2025

SJU-BWI

In general, everything was nice.

6.0 Okay

Verified traveler, Apr 2025

MCO-ACY

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

8.0 Very good

Verified traveler, Apr 2025

LGA-DFW

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

10.0 Wonderful

Leo, Apr 2025

FLL-MSY

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

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$45 Find Cheap Spirit Airlines Flights from Boston to Chicago

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Cheap Spirit Airlines Flight Deals from Boston to Chicago

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Good to know

When to Book Flights with Spirit Airlines from Boston to Chicago

FAQs for flying to Chicago with Spirit Airlines

How far in advance should I book tickets for a flight with Spirit Airlines from Boston to Chicago?

Is Spirit Airlines the cheapest airline to fly with from Boston to Chicago?

What is the cheapest Spirit Airlines flight from Boston to Chicago?

Does Spirit Airlines fly direct to Chicago from Boston?

What’s the cheapest day of the week to fly from Boston to Chicago with Spirit Airlines?

What’s the cheapest month to fly from Boston to Chicago with Spirit Airlines?

Spirit Airlines Customer Reviews

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Everything you need to know for your flight from Boston to Chicago

Other airlines flying from Boston to Chicago

Flights from the other most popular airlines that fly from Boston to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.

Cabin class types available on flights to Chicago

Cabin classes available on flights to Boston. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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