Flights from Chicago to Boston
CHI
Chicago
5h 37m avg
BOS
Boston
Flights from
$169
Compare 1 options across 1 airline
Updated 2 months ago
$169
Cheapest Flight
$169
Average Price
0
Direct Flights
1
Airlines
Compare All CHI to BOS Flights
Prices are per person for one-way travel. Click “Book” to complete your reservation on the partner site.
1 of 1 flight
| Airline | Schedule | Stops | Duration | Price | |
|---|---|---|---|---|---|
AA
AA · 966
|
06:00
CHI
11:37
BOS
|
0 stop(s) | 5h 37m | $169 Best | Book → |
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Airport Information
Key details about departure and arrival airports for this route
BOS
Boston Logan International Airport
City: Boston
Country: US
Type: Large Airport
Elevation: 20 ft
BOS Airport Guide →
Country: US
Type: Large Airport
Elevation: 20 ft
Tips for Chicago to Boston Flights
Save money and travel smarter with these route-specific tips
When to Book
Book CHI–BOS flights 6–8 weeks in advance for the best prices. Last-minute fares are typically 40–60% more expensive on this route.
Price Trends
The average fare is $169, but prices as low as $169 are available.
Direct vs Connecting
No direct flights currently listed. Consider flexible dates or nearby airports for better connections.
Flexible Dates
Flying midweek (Tuesday–Thursday) on CHI–BOS is typically 15–30% cheaper. Use our price comparison to spot the best day to fly.
Top Hotels in Boston
Book accommodation at your destination — top-rated stays near BOS airport
Frequently Asked Questions
Everything you need to know about flying CHI to BOS
What is the cheapest flight from Chicago to Boston?
The cheapest flight from Chicago (CHI) to Boston (BOS) currently starts at $169 with AA. Prices are updated regularly and may vary by date and availability.
How many airlines fly from CHI to BOS?
We found 1 airline(s) operating on the CHI–BOS route, including AA.
Are there direct flights from Chicago to Boston?
No direct flights are currently listed on this route. All available options involve at least one stop. Consider flexible dates or nearby airports for better connection options.
What is the average flight price on this route?
The average flight price from Chicago to Boston is approximately $169. Prices range from $169 to $169 depending on airline, time, and class.
How long is the flight from CHI to BOS?
The average flight duration from Chicago to Boston is approximately 5 hours 37 minutes. Direct flights are typically shorter than connecting options.
What is the baggage allowance on CHI–BOS flights?
Baggage allowance varies by airline and fare class. Most economy fares on this route include 1 carry-on (7–8 kg) and 1 checked bag (20–23 kg). Always confirm baggage rules on the airline's site at booking — low-cost carriers may charge for checked bags.
From
$169
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