If you are looking for a chance to travel to Illinois, here’s a great opportunity for you! If so, you can get a round-trip flight with United Airlines from Boston to Chicago starting at $86. Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. The city is also renowned for its museums, including the Art Institute of Chicago with its noted Impressionist and Post-Impressionist works. Take advantage of this flight deal and book your flight today!
We recommend you look up your preferred dates on Google Flights in case there is a cheaper price than the ones we listed. Depending when you book, the prices can change! (YMMV) The airline fares rule associated with your flight and be reviewed over pre-purchase, on your contract, and post purchase with the itinerary displayed on their website, be sure you read their full terms before making your purchase.
Flights from Boston to Chicago
- Buy It Now
- Promotion: Round-trip from Boston to Chicago starting at $86
- Routes: From Boston, Massachussetts to Chicago, Illinois
- Distance: 1,728 miles
- Valid: Valid for travel until early November for Tuesday, Wednesday and Saturday departure and returns. Availability is limited. Must purchase at least 21 days in advance of departure.
- Terms: Prices shown based on searches made in the last 24 hours. Due to constant changing availability, these fares may no longer be available. For FAQ you can contact your airlines at their Help page. Baggage fees are not included in your trip cost unless otherwise stated and will be charged directly by the airline at check-in. Please visit your chosen carrier to review all fare cost including taxes and baggage fees. Purchases must be made at least 2 weeks in advance of departure.
How To Get BOS/ORD Flight Deal:
- Use Priceline to check the flights and times that fit best for you. We recommend selecting United Airlines since their prices seem to be the cheapest. (YMMV)
- To earn cash back we highly recommend using AMEX Premier Rewards Gold Card to save the most money.
- Once you found the times that you would like to make sure you book it early so that it doesn’t change.
This is a great trip to take a vacation! Plan early in order to receive this benefit. I highly recommend going so you can experience a new part of the world! Make sure you use your Citi Hilton HHonors Visa Signature Card to save the maximum amount of money! This card is great for traveling anywhere. US citizens should visit the US Passports & International Travel website for the latest information, including exercising safety abroad and entry requirements. This is the cheapest fare I found but please let us know if you got anything different! If you want more Cheap Flight Deals, check out our master list!
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