Boston (BOS) to Chicago (ORD): Award Flights with Points & Miles
Also see: Chicago → Boston
The 866-mile flight from Boston to Chicago takes about 3h nonstop on American Airlines, Delta Airlines, JetBlue, United Airlines. Below is the full award chart for this route across 24 frequent flyer programs — the lowest published one-way price in each cabin, so you can see exactly which miles get you there for the least.
Boston to Chicago Award Chart: All 24 Programs
Lowest published one-way award price per cabin. “Dynamic” means the program prices this route based on cash fares rather than a fixed chart.
| Program | Economy | Prem. Economy | Business | First | Bookable Airlines |
|---|---|---|---|---|---|
| American Airlines AAdvantage | 5,500 | — | 12,500 | 32,500 | American Airlines |
| Alaska Airlines Atmos Rewards | 7,500 | 10,000 | 15,000 | 25,000 | American Airlines |
| Qatar Airways Privilege Club | 8,500 | — | 17,000 | 33,000 | American Airlines, JetBlue |
| Virgin Atlantic Flying Club | 11,000 | 26,000 | 11,000 | — | Delta Airlines |
| Emirates Skywards | 12,000 | — | 35,000 | — | United Airlines |
| Etihad Guest | 12,000 | 13,000 | 25,000 | 40,000 | American Airlines, JetBlue |
| Qantas Frequent Flyer | 13,800 | 21,600 | 29,000 | 43,600 | American Airlines |
| Air Canada Aeroplan | 15,000 | — | 30,000 | — | United Airlines |
| ANA Mileage Club | 15,000 | — | 27,500 | 45,000 | United Airlines |
| Cathay Pacific Asia Miles | 15,000 | 25,000 | 33,000 | 53,000 | American Airlines |
| Singapore Airlines KrisFlyer | 15,000 | — | 29,000 | 43,000 | United Airlines |
| Turkish Airlines Miles&Smiles | 15,000 | — | 22,500 | 30,000 | United Airlines |
| United MileagePlus | 15,000 | Dynamic | 30,000 | Dynamic | JetBlue, United Airlines |
| Finnair Plus | 16,500 | — | — | 40,000 | American Airlines |
| Thai Airways Royal Orchid Plus | 17,500 | 22,500 | 27,500 | 35,000 | United Airlines |
| British Airways Executive Club | 18,000 | — | 35,500 | 35,500 | American Airlines |
| Eva Air Infinity MileageLands | 19,500 | — | 29,000 | 38,500 | United Airlines |
| Japan Airlines Mileage Bank | 24,000 | 24,000 | 24,000 | 24,000 | American Airlines |
| TAP Air Portugal Miles&Go | 30,000 | — | 45,000 | 60,000 | United Airlines |
| Avianca Lifemiles | Dynamic | Dynamic | Dynamic | Dynamic | United Airlines |
| Delta Skymiles | Dynamic | Dynamic | Dynamic | Dynamic | Delta Airlines |
| Flying Blue | Dynamic | Dynamic | Dynamic | Dynamic | Delta Airlines |
| Iberia Plus | Dynamic | Dynamic | Dynamic | Dynamic | American Airlines |
| JetBlue TrueBlue | Dynamic | Dynamic | Dynamic | Dynamic | JetBlue, United Airlines |
Prices are published saver-level award chart rates and exclude taxes, fees, and carrier surcharges. Programs update charts without notice — verify with the program before transferring points.
Booking Tips: Boston to Chicago on Points
- 1Best business class value: Virgin Atlantic Flying Club at 11,000 miles one-way (transfer from Amex Membership Rewards, Chase Ultimate Rewards, Bilt Rewards).
- 2Cheapest economy award: 5,500 miles with American Airlines AAdvantage. Compare cash fares before redeeming — short on points value, economy is sometimes better paid in cash.
- 3Prices shown are the lowest published one-way saver rates. Peak dates, partner surcharges, and taxes/fees vary by program — always compare the final out-of-pocket total.
- 4Avianca Lifemiles, Delta Skymiles, Flying Blue price this route dynamically — their cost tracks cash fares, so watch for flash sales and off-season dates.
- 5Award space at saver level is limited on most airlines. Booking 3–11 months ahead, flying midweek, and checking nearby airports all improve your odds.
See live award options for Boston to Chicago
The table above shows published chart rates. Run a search to compare every program and routing for your dates — including transfer bonuses.
Search This RouteFrequently Asked Questions
How many miles do I need to fly from Boston to Chicago?
One-way economy awards from Boston to Chicago start at 5,500 miles with American Airlines AAdvantage. Business class starts at 11,000 miles with Virgin Atlantic Flying Club. Exact pricing depends on the program, airline, and travel dates.
What is the cheapest way to book Boston to Chicago in business class with points?
Virgin Atlantic Flying Club has the lowest published business class rate at 11,000 miles one-way. You can top up this program by transferring from Amex Membership Rewards, Chase Ultimate Rewards, Bilt Rewards, Capital One Miles, Citi ThankYou, Marriott Bonvoy, Rove Miles. Award availability at saver levels is limited, so flexible dates help.
How many points is first class from Boston to Chicago?
First class awards on this route start at 24,000 miles one-way via Japan Airlines Mileage Bank. First class award space is scarce — book as soon as schedules open when possible.
Which airlines fly from Boston to Chicago?
Airlines with nonstop service between Boston and Chicago include American Airlines, Delta Airlines, JetBlue, United Airlines. The flight covers about 866 miles and takes roughly 3h nonstop. Additional partner airlines serve the route with one connection.
Which credit card points can I use to fly from Boston to Chicago?
Most major transferable currencies work for this route. Amex Membership Rewards, Chase Ultimate Rewards, Citi ThankYou, Capital One Miles, and Bilt Rewards each transfer to multiple programs listed in the award chart above — compare the programs your points transfer to before booking.