Cheap flights from Chicago to Boston from $154 MDW, ORD, RFD → BOS

Found recently, and the cheapest we hold

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $204 to $378.

At $478, the cheapest return found recently is above that range.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

We hold no other 5-night return fares leaving within 3 days of 24 Nov to compare.

Every date we hold

7 fares on 3 departure dates

Which month looks cheapest?

November 2026 is the cheapest month — from $249.

Found recently, and the cheapest we hold

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $86 to $179.

Those were the prices on those days, not today's.

Could nearby dates be cheaper?

No. We hold one-way fares on 2 other departure dates within 3 days of 21 Nov, and none is cheaper.

Every date we hold

8 fares on 5 departure dates

Which month looks cheapest?

November 2026 is the cheapest month — from $143.

Return

Fares 14 to 29 days before departure were typically 39% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

One-way

Fares 14 to 29 days before departure were typically 29% lower than 7 to 13 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (49 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

How much is a return flight from Chicago to Boston?

The cheapest return found recently is $478 with Frontier Airlines, 24 Nov to 29 Nov, found 4 days ago. The cheapest return we hold, of any age, is $249 with jetBlue, 21 Nov to 22 Nov, found 7 days ago. The cheapest return fare on each of 3 departure dates is usually $269 to $383.

How much is a one-way flight from Chicago to Boston?

The cheapest one-way found recently is $154 with Southwest Airlines, 21 Nov, found 2 days ago. The cheapest one-way we hold, of any age, is $143 with Southwest Airlines, 21 Nov, found 5 days ago. The cheapest one-way fare on each of 5 departure dates is usually $155 to $172.

What is the cheapest month to fly from Chicago to Boston?

November 2026 is the cheapest month for a return, from $249, 21 Nov to 22 Nov, found 7 days ago. It is the cheapest month for a one-way too, from $143, 21 Nov, found 5 days ago.

How far ahead should I book a flight from Chicago to Boston?

In 49 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 39% lower than 0 to 6 days before departure. One-way fares 14 to 29 days before departure were typically 29% lower than 7 to 13 days before departure.

Is there a direct flight from Chicago to Boston?

Yes, the cheapest nonstop return found recently is $277 with Southwest Airlines, 21 Nov to 22 Nov, found 5 days ago. The cheapest nonstop one-way found recently is $154 with Southwest Airlines, 21 Nov, found 2 days ago.

How long is the flight from Chicago to Boston?

The cheapest nonstop one-way found recently, with Southwest Airlines on 21 Nov, takes 2 h 20 min from Chicago Midway International Airport (MDW) to Logan International Airport (BOS).

Which airlines have the cheapest flights from Chicago to Boston?

Between 21 Nov and 1 Jan 2027, jetBlue has the cheapest return on 2 of the 3 departure dates we hold, and Frontier Airlines on 1. Between 19 Nov and 23 Sept 2027, Southwest Airlines has the cheapest one-way on 2 of the 5 departure dates we hold, American Airlines on 2 and Frontier Airlines on 1.