$71 Cheap flight deals from Boston (BOS) to Evanston (CHI)

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This Weekend's Flight Deals from Boston to Evanston

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.

Sun, Jul 12 - Sat, Jul 18
BOS
Logan Intl.
RFD
Greater Rockford
$244 Roundtrip, found 5 days ago
$244
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Jul 12 from Logan Intl. to Greater Rockford, returning Sat, Jul 18, priced at $244 found 5 days ago
Sun, Jul 12 - Fri, Jul 24
BOS
Logan Intl.
MDW
Midway Intl.
$262 Roundtrip, found 7 hours ago
$262
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sun, Jul 12 from Logan Intl. to Midway Intl., returning Fri, Jul 24, priced at $262 found 7 hours ago
Sun, Jul 12 - Mon, Jul 13
BOS
Logan Intl.
ORD
O'Hare Intl.
$293 Roundtrip, found 2 hours ago
$293
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Sun, Jul 12 from Logan Intl. to O'Hare Intl., returning Mon, Jul 13, priced at $293 found 2 hours ago
Sat, Jul 11 - Tue, Jul 14
MHT
Manchester-Boston Regional
ORD
O'Hare Intl.
$456 Roundtrip, found 3 days ago
$456
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 11 from Manchester-Boston Regional to O'Hare Intl., returning Tue, Jul 14, priced at $456 found 3 days ago

Airfares from $71 One Way, $141 Round Trip from Boston to Evanston

Prices starting at $141 for return flights and $71 for one-way flights to Evanston were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Sep 24 - Sat, Sep 26
BOS
Boston
RFD
Rockford
$141 Roundtrip, found 21 hours ago
$141
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Thu, Sep 24 from Boston to Rockford, returning Sat, Sep 26, priced at $141 found 21 hours ago
Wed, Aug 12 - Mon, Aug 17
BOS
Boston
MDW
Chicago
$145 Roundtrip, found 5 hours ago
$145
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Aug 12 from Boston to Chicago, returning Mon, Aug 17, priced at $145 found 5 hours ago
Thu, Sep 24 - Sat, Sep 26
ORH
Worcester
ORD
Chicago
$192 Roundtrip, found 21 hours ago
$192
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Thu, Sep 24 from Worcester to Chicago, returning Sat, Sep 26, priced at $192 found 21 hours ago
Fri, Sep 11 - Thu, Sep 17
PVD
Providence
ORD
Chicago
$214 Roundtrip, found 6 hours ago
$214
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Fri, Sep 11 from Providence to Chicago, returning Thu, Sep 17, priced at $214 found 6 hours ago
Wed, Oct 14 - Sat, Oct 17
MHT
Manchester
MDW
Chicago
$221 Roundtrip, found 10 hours ago
$221
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Wed, Oct 14 from Manchester to Chicago, returning Sat, Oct 17, priced at $221 found 10 hours ago

Evanston economy flight packages

Price found within the past 48 hours. Click for updated prices.
Wind Creek Southland Casino and Hotel
4.0-star property

Wind Creek Southland Casino and Hotel

9.4/10 Exceptional! (467 reviews)

Aug 28 - Aug 31

3 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Coach
Save 100% on your flight
Price was $589, price is now $417 per person
$417
per person
found 1 day ago
The rooms were very clean and anytime that you asked for anything. Example, extra towels they were given to you right away. I was there to attend Mileston Tchula classroom reunion, and the staff that was assigned to that event I’m giving five stars. They were the greatest. Thank you guys so very much.

Reviewed on Jul 9, 2026

Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,809 reviews)

Aug 28 - Aug 31

3 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Coach
Save 100% on your flight
Price was $744, price is now $488 per person
$488
per person
found 1 day ago
Great hotel, close to a lot of tourist attractions literally walked to the bean and magnificent mile Hotel had breakfast but not that fancy but I would definitely recommend this hotel

Reviewed on Jul 9, 2026

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (497 reviews)

Aug 14 - Aug 16

2 night stay

Boston (BOS) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Boston (BOS)

American Airlines • Coach
Save 100% on your flight
Price was $1,179, price is now $820 per person
$820
per person
found 1 day ago
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on Jul 9, 2026

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More About Flying To Evanston from Boston

Route Information for Flights from Boston to Evanston

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

Boston to Evanston

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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.