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popularserra | Staff posted May 04, 2026 01:56 PM
popularserra | Staff posted May 04, 2026 01:56 PM

Summer Round Trip Boston - Chicago or Vice Versa $167 Nonstop Airfares (Travel June - September 2026)

$167

Expedia
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United, JetBlue, American Airlines, Delta Air Lines and Expedia have round trip airfares travelling to and from Chicago (ORD) and Boston (BOS) for $167, nonstop. These are basic economy fares. On American, Delta and JetBlue you may have a personal item and a carry-on bag. On United, you may only have a carry-on bag.

Travel Availability:
Departs BOS: June 2-3, 6, 9-10, 16-17, 23-24 30; July 1, 7-8, 14-15, 21-22, 28; Aug 4-5, 11-12, 18-19, 25-26; Sept 1-2, 8
Departs ORD: June 2-3, 6, 9-10, 16-17, 23-24, 30; July 1, 7-8, 14-15, 21-22, 28-29; Aug 4-5, 11-12, 18-19, 25-26; Sept 1-2, 8

To book this deal, use dates and book flights with Expedia [expedia.com], American Airlines [aa.com], JetBlue [jetblue.com], United Airlines [united.com] or Delta Air Lines [delta.com]. Want to see more travel deals? Click here or here. Disclaimer: List price is an estimate and subject to fluctuate based on air carrier/hotel location, flight times/season or travel dates.


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Community Notes
About the Poster
Deal Details
Community Notes
About the Poster
United, JetBlue, American Airlines, Delta Air Lines and Expedia have round trip airfares travelling to and from Chicago (ORD) and Boston (BOS) for $167, nonstop. These are basic economy fares. On American, Delta and JetBlue you may have a personal item and a carry-on bag. On United, you may only have a carry-on bag.

Travel Availability:
Departs BOS: June 2-3, 6, 9-10, 16-17, 23-24 30; July 1, 7-8, 14-15, 21-22, 28; Aug 4-5, 11-12, 18-19, 25-26; Sept 1-2, 8
Departs ORD: June 2-3, 6, 9-10, 16-17, 23-24, 30; July 1, 7-8, 14-15, 21-22, 28-29; Aug 4-5, 11-12, 18-19, 25-26; Sept 1-2, 8

To book this deal, use dates and book flights with Expedia [expedia.com], American Airlines [aa.com], JetBlue [jetblue.com], United Airlines [united.com] or Delta Air Lines [delta.com]. Want to see more travel deals? Click here or here. Disclaimer: List price is an estimate and subject to fluctuate based on air carrier/hotel location, flight times/season or travel dates.


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May 04, 2026 02:03 PM
3,499 Posts
Joined Feb 2008
overzeetopMay 04, 2026 02:03 PM
3,499 Posts
Might be a cheap way to travel for those in Chicago to come east and see the Tall Ships July 11–16, 2026 in Boston harbor if the flight times allow and you can take off mid-week.
May 04, 2026 06:00 PM
26 Posts
Joined Dec 2006
ZenMysteryMay 04, 2026 06:00 PM
26 Posts
Certainly cheap for a round trip.
May 04, 2026 08:42 PM
608 Posts
Joined Mar 2006
weirdlyMay 04, 2026 08:42 PM
608 Posts
Beats the bus!
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May 05, 2026 12:07 AM
92,391 Posts
Joined Jul 2004
serraMay 05, 2026 12:07 AM
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92,391 Posts
yep....works both ways

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