$53 Cheap flight deals from Boston (BOS) to Glenview (CHI)

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This Weekend's Flight Deals from Boston to Glenview

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, Jan 18 - Sun, Jan 25
BOS
Logan Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 1 hour ago
$135
Roundtrip
found 1 hour ago
Select United flight, departing Sun, Jan 18 from Logan Intl. to O'Hare Intl., returning Sun, Jan 25, priced at $135 found 1 hour ago
Sat, Jan 17 - Tue, Jan 20
BOS
Logan Intl.
MDW
Midway Intl.
$140 Roundtrip, found 2 days ago
$140
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Logan Intl. to Midway Intl., returning Tue, Jan 20, priced at $140 found 2 days ago
Sat, Jan 17 - Tue, Jan 20
BOS
Logan Intl.
RFD
Greater Rockford
$141 Roundtrip, found 2 days ago
$141
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jan 17 from Logan Intl. to Greater Rockford, returning Tue, Jan 20, priced at $141 found 2 days ago
Sun, Jan 18 - Sun, Jan 25
PVD
T.F. Green
ORD
O'Hare Intl.
$265 Roundtrip, found 5 days ago
$265
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sun, Jan 18 from T.F. Green to O'Hare Intl., returning Sun, Jan 25, priced at $265 found 5 days ago

Airfares from $53 One Way, $105 Round Trip from Boston to Glenview

Prices starting at $105 for return flights and $53 for one-way flights to Glenview were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Feb 9 - Wed, Feb 11
BOS
Boston
MDW
Chicago
$105 Roundtrip, found 1 day ago
$105
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Feb 9 from Boston to Chicago, returning Wed, Feb 11, priced at $105 found 1 day ago
Wed, Feb 4 - Thu, Feb 5
BOS
Boston
ORD
Chicago
$105 Roundtrip, found 1 day ago
$105
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Feb 4 from Boston to Chicago, returning Thu, Feb 5, priced at $105 found 1 day ago
Mon, Apr 27 - Wed, Apr 29
BOS
Boston
RFD
Rockford
$139 Roundtrip, found 4 hours ago
$139
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Mon, Apr 27 from Boston to Rockford, returning Wed, Apr 29, priced at $139 found 4 hours ago
Thu, Apr 23 - Fri, Apr 24
ORH
Worcester
ORD
Chicago
$155 Roundtrip, found 4 days ago
$155
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Apr 23 from Worcester to Chicago, returning Fri, Apr 24, priced at $155 found 4 days ago
Mon, May 4 - Tue, May 12
PVD
Providence
ORD
Chicago
$187 Roundtrip, found 2 hours ago
$187
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Mon, May 4 from Providence to Chicago, returning Tue, May 12, priced at $187 found 2 hours ago

Glenview economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,229 reviews)

Feb 9 - Feb 13

4 night stay

Boston (BOS) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Price was $437, price is now $334 per person
$334
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 13 - Feb 15

2 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • Coach
Price was $653, price is now $415 per person
$415
per person
found 1 day ago
Staff is TOP NOTCH! I am in a wheelchair right now, recovering from a knee surgery, and staff could not have been more solicitous and helpful. Also, when we checked in, upon learning of my daughter‘s birthday on Christmas, the front desk representative gave us a complementary room upgrade and sent up chocolates! The room was very clean and the shower was fantastic. Not enough good words about the buffet, as long as you’re clear that it is a “breakfast“ buffet and not a “brunch“ buffet :-). I think I was expecting a sliced roast beef and an omelette bar, but it is in fact a very extensive selection of breakfast foods. The restaurant recommendation was spot on. We had a delicious dinner of fine Mediterranean/Sardinian foodat Nora’s next door and enjoyed it immensely. I have now joined the capital RIU club and plan on spending much more time at their other properties, particularly in Costa Rica, where I am moving next month. Kudos to all, and thank you for our wonderful stay!

Reviewed on Dec 28, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Feb 13 - Feb 15

2 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • Coach
Price was $849, price is now $644 per person
$644
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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Glenview packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago - North Shore Conference Center
4.0-star property

DoubleTree by Hilton Chicago - North Shore Conference Center

8.8/10 Excellent! (1,002 reviews)

Feb 20 - Feb 23

3 night stay

Boston (BOS) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $530, price is now $428 per person
$428
per person
found 1 day ago
Hosting friends from out of town. Great place.

Reviewed on Nov 28, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG
3.0-star property

Holiday Inn Chicago O'Hare – Rosemont by IHG

9/10 Wonderful! (2,591 reviews)

Feb 20 - Feb 23

3 night stay

Boston (BOS) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $544, price is now $436 per person
$436
per person
found 1 day ago
Very nice staff. Clean room, and nice restaurant and coffee bar in the lobby. I have stayed there several times. It's a convinient location as well.

Reviewed on Dec 29, 2025

Hilton Rosemont Chicago O'Hare
3.5-star property

Hilton Rosemont Chicago O'Hare

8.4/10 Very Good! (1,000 reviews)

Feb 20 - Feb 23

3 night stay

Boston (BOS) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $631, price is now $512 per person
$512
per person
found 1 day ago
Good hotel close to airport, with free airport shuttle, 7-10 min away. Quite convenient

Reviewed on Nov 4, 2025

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More About Flying To Glenview from Boston

Route Information for Flights from Boston to Glenview

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

Boston to Glenview

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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.