$41 Cheap flight deals from Boston (BOS) to Historic Route 66 (CHI)

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This Weekend's Flight Deals from Boston to Historic Route 66

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Feb 7 - Tue, Feb 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 8 hours ago
$127
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Feb 7 from Logan Intl. to O'Hare Intl., returning Tue, Feb 10, priced at $127 found 8 hours ago
Fri, Feb 6 - Sun, Feb 8
BOS
Logan Intl.
MDW
Midway Intl.
$150 Roundtrip, found 2 days ago
$150
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Feb 6 from Logan Intl. to Midway Intl., returning Sun, Feb 8, priced at $150 found 2 days ago
Sat, Feb 7 - Fri, Feb 20
PVD
T.F. Green
MDW
Midway Intl.
$511 Roundtrip, found 3 days ago
$511
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Feb 7 from T.F. Green to Midway Intl., returning Fri, Feb 20, priced at $511 found 3 days ago
Fri, Feb 6 - Tue, Feb 24
BOS
Logan Intl.
TUL
Tulsa Intl.
$554 Roundtrip, found 5 days ago
$554
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Feb 6 from Logan Intl. to Tulsa Intl., returning Tue, Feb 24, priced at $554 found 5 days ago

Airfares from $41 One Way, $99 Round Trip from Boston to Historic Route 66

Prices starting at $99 for return flights and $41 for one-way flights to Historic Route 66 were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Apr 11 - Mon, Apr 13
BOS
Boston
ORD
Chicago
$99 Roundtrip, found 8 hours ago
$99
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Apr 11 from Boston to Chicago, returning Mon, Apr 13, priced at $99 found 8 hours ago
Fri, May 1 - Sat, May 2
BOS
Boston
MDW
Chicago
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, May 1 from Boston to Chicago, returning Sat, May 2, priced at $100 found 1 day ago
Mon, Feb 23 - Mon, Mar 2
BOS
Boston
OKC
Oklahoma City
$169 Roundtrip, found 15 hours ago
$169
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Boston to Oklahoma City, returning Mon, Mar 2, priced at $169 found 15 hours ago
Sat, Apr 25 - Thu, Apr 30
BOS
Boston
STL
St. Louis
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Apr 25 from Boston to St. Louis, returning Thu, Apr 30, priced at $187 found 1 day ago
Mon, Jun 1 - Tue, Jun 9
ORH
Worcester
ORD
Chicago
$193 Roundtrip, found 3 days ago
$193
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Jun 1 from Worcester to Chicago, returning Tue, Jun 9, priced at $193 found 3 days ago

Historic Route 66 economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Mar 5 - Mar 7

2 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $396, price is now $273 per person
$273
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

The Inn at Vanessie
4.5-star property

The Inn at Vanessie

8.8/10 Excellent! (1,001 reviews)

Mar 13 - Mar 17

4 night stay

Boston (BOS) to Albuquerque (ABQ)

American Airlines • Non-stop roundtrip • Coach
Price was $929, price is now $655 per person
$655
per person
found 1 day ago
Everything was fantastic. The staff is totally awesome. The room was beautiful total southwest looking the whole place is Adobe style and real Adobe building. If you want a real Southwest experience come to this Inn. One thing you have to understand is that it really is Southwest Adobe hotel/lnn. Do not expected to be a Hilton or the likes. It’s the real mcCoy and it’s fantastic. Walking distance you’re about eight minutes from the plaza and driving your maybe three or four minutes at the most. We definitely are coming back here in the future

Reviewed on Dec 12, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Mar 12 - Mar 15

3 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,208, price is now $863 per person
$863
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

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More About Flying To Historic Route 66 from Boston

Route Information for Flights from Boston to Historic Route 66

Origin Airport IATA Code
BOS
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Boston to Historic Route 66

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Get Bargain Fares for Boston to Historic Route 66 Flights

Orbitz makes it quick and easy to find airfare sales and low fare tickets. Decide which airline and flight times you want or, if your schedule is flexible, choose a range of dates to see the best prices.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.