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American Airlines flights from Boston to Chicago (BOS - CHI)

BOS — CHI
May 29 — Jun 51
From?
To?
Wed 5/29
Wed 6/5
1 adult, Economy
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Cheapflights users flying from Boston to Chicago on American Airlines typically fly into Chicago O'Hare Intl and depart from Boston Logan Intl. Select your dates above for pricing.

American Airlines flights from Boston to Chicago in 2024

Find detailed information about American Airlines flights from Boston to Chicago. Explore the options provided by American Airlines to plan your journey from Boston to Chicago. Data last updated May 24, 2024.

Popular in

June

Cheapest in

January

Average price (all airlines)

$302

One-way from

$58

Round-trip from

$136
Highest demand for flights from Boston Logan Intl to Chicago; 13% potential price increase.
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Best time to find cheap flights from Boston Logan Intl to Chicago; 1% potential price drop.
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Average price for all Boston Logan Intl to Chicago flights (one-way and round-trip).
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Cheapest one-way American Airlines flight from Boston Logan Intl to Chicago
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Cheapest round-trip American Airlines flight from Boston Logan Intl to Chicago
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  • Can I get a flight from Boston to Chicago on American Airlines for under $400?

    American Airlines offers 18 flights from Boston to Chicago for under $400. Prices vary by date and time. To see all prices and select your dates, click here.

  • How do most travelers feel about American Airlines?

    9,175 Cheapflights users have left reviews for American Airlines and have rated the airline 8.0/10. If you are looking to travel from Boston to Chicago on American Airlines, input your dates in the form above for our best prices!

Cheapest American Airlines flights from Boston to Chicago

Discover the cheapest flight options specifically offered by American Airlines for travel from Boston to Chicago. Compare prices and availability to find the most affordable fares for your desired travel dates. These prices are based on average fares users found. In the last 7 days, Cheapflights users made a total of 2,725,499 searches. The data was last updated on May 24, 2024.
Wed 6/125:18 amBOS - ORD
Nonstop2h 55mAmerican Airlines
Tue 6/186:45 amORD - BOS
Nonstop2h 26mAmerican Airlines
Deal found 5/23$136
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Sat 6/155:18 amBOS - ORD
Nonstop2h 55mAmerican Airlines
Wed 6/198:36 pmORD - BOS
Nonstop2h 25mAmerican Airlines
Deal found 5/22$145
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Tue 6/47:10 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Tue 6/116:45 amORD - BOS
Nonstop2h 26mAmerican Airlines
Deal found 5/23$160
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Direct flights from Boston to Chicago on American Airlines

Discover the cheapest flight options specifically offered by American Airlines for travel from Boston to Chicago. Compare prices and availability to find the most affordable fares for your desired travel dates. These prices are based on average fares users found. In the last 7 days, Cheapflights users made a total of 2,725,499 searches. The data was last updated on May 24, 2024.
Wed 6/125:18 amBOS - ORD
Nonstop2h 55mAmerican Airlines
Tue 6/186:45 amORD - BOS
Nonstop2h 26mAmerican Airlines
Deal found 5/23$136
Pick Dates
Sat 6/155:18 amBOS - ORD
Nonstop2h 55mAmerican Airlines
Wed 6/198:36 pmORD - BOS
Nonstop2h 25mAmerican Airlines
Deal found 5/22$145
Pick Dates
Wed 8/147:30 pmBOS - ORD
Nonstop2h 56mAmerican Airlines
Sat 8/176:00 amORD - BOS
Nonstop2h 18mAmerican Airlines
Deal found 5/23$147
Pick Dates

Last minute deals on Cheapflights

Explore last-minute flight deals on American Airlines for various destinations, including Boston to Chicago. Discover attractive deals on flights departing soon. Keep an eye on the latest last-minute deals to find great opportunities for spontaneous travel. Please note that prices are subject to change and availability may vary. Data last updated May 24, 2024 and based on user searches. In the last 7 days, Cheapflights users made a total of 2,725,499 searches.
Sun 6/25:25 amBOS - ORD
Nonstop2h 52mAmerican Airlines
Fri 6/78:36 pmORD - BOS
Nonstop2h 25mAmerican Airlines
Deal found 5/22$176
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Sun 6/25:25 amBOS - ORD
Nonstop2h 52mAmerican Airlines
Tue 6/46:55 pmORD - BOS
Nonstop2h 30mAmerican Airlines
Deal found 5/22$180
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Sun 6/25:25 amBOS - ORD
Nonstop2h 52mAmerican Airlines
Tue 6/48:29 pmORD - BOS
Nonstop2h 26mAmerican Airlines
Deal found 5/23$181
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One-way American Airlines flights to Chicago from Boston

Search for one-way flight options from Boston to Chicago specifically provided by American Airlines. Find affordable one-way fares from American Airlines and compare prices with other airlines. These prices are based on average fares users found. In the last 7 days, Cheapflights users made a total of 2,725,499 searches. The data was last updated on May 24, 2024.
Tue 6/255:18 amBOS - ORD
Nonstop2h 55mAmerican Airlines
Deal found 5/23$58
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Tue 7/95:15 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 5/23$69
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Sat 8/177:30 pmBOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 5/23$79
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Best time to book a flight from Boston to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Boston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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Fly from Boston to Chicago on another airline
Consider alternative airlines that service the Chicago area. Flight routes are based on user searches made on Cheapflights and were last updated on May 24, 2024.

Delta flights from Boston Logan Intl to Chicago
United Airlines flights from Boston Logan Intl to Chicago

See what others are saying about American Airlines

Read reviews and see what other travelers are saying about their experiences with American Airlines. Get insights from real passengers regarding the airline's services, customer satisfaction, and overall travel experience. Use these reviews to inform your decision when choosing American Airlines for your next flight. Reviews last updated May 24, 2024.
American Airlines
7.3
Good
14,388 reviews
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Overview

Food

6.6

Entertainment

7.1

Boarding

7.6

Crew

8.0

Comfort

7.2
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