$59 Cheap flight deals from Boston (BOS) to Cicero (CHI)

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This Weekend's Flight Deals from Boston to Cicero

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 4 - Sun, Jan 11
BOS
Logan Intl.
RFD
Greater Rockford
$159 Roundtrip, found 7 hours ago
$159
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sun, Jan 4 from Logan Intl. to Greater Rockford, returning Sun, Jan 11, priced at $159 found 7 hours ago
Sat, Jan 3 - Sat, Jan 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 7 hours ago
$177
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, Jan 3 from Logan Intl. to O'Hare Intl., returning Sat, Jan 10, priced at $177 found 7 hours ago
Sat, Jan 3 - Sat, Jan 10
BOS
Logan Intl.
MDW
Midway Intl.
$202 Roundtrip, found 7 hours ago
$202
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, Jan 3 from Logan Intl. to Midway Intl., returning Sat, Jan 10, priced at $202 found 7 hours ago
Sat, Jan 3 - Tue, Jan 20
PVD
T.F. Green
ORD
O'Hare Intl.
$475 Roundtrip, found 3 days ago
$475
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jan 3 from T.F. Green to O'Hare Intl., returning Tue, Jan 20, priced at $475 found 3 days ago

Airfares from $59 One Way, $111 Round Trip from Boston to Cicero

Prices starting at $111 for return flights and $59 for one-way flights to Cicero 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, Jan 24 - Sun, Jan 25
BOS
Boston
MDW
Chicago
$111 Roundtrip, found 4 days ago
$111
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Jan 24 from Boston to Chicago, returning Sun, Jan 25, priced at $111 found 4 days ago
Sun, Feb 8 - Mon, Feb 9
BOS
Boston
ORD
Chicago
$117 Roundtrip, just found
$117
Roundtrip
just found
Select United flight, departing Sun, Feb 8 from Boston to Chicago, returning Mon, Feb 9, priced at $117 just found
Sun, Jan 25 - Sun, Feb 1
BOS
Boston
ORD
Chicago
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Jan 25 from Boston to Chicago, returning Sun, Feb 1, priced at $117 found 1 day ago
Mon, Apr 27 - Wed, Apr 29
BOS
Boston
RFD
Rockford
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Apr 27 from Boston to Rockford, returning Wed, Apr 29, priced at $139 found 2 days ago
Fri, Jan 9 - Sun, Jan 11
ORH
Worcester
ORD
Chicago
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jan 9 from Worcester to Chicago, returning Sun, Jan 11, priced at $158 found 1 day ago

Cicero 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)

Feb 12 - Feb 16

4 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Coach

Chicago (ORD) to Boston (BOS)

American Airlines • Coach
Save 100% on your flight
Price was $660, price is now $441 per person
$441
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

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (2,947 reviews)

Feb 12 - Feb 16

4 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Coach

Chicago (ORD) to Boston (BOS)

American Airlines • Coach
Save 100% on your flight
Price was $661, price is now $444 per person
$444
per person
found 1 day ago
Staff was friendly. Rooms are showing their age. No pool, no sauna, nothing really fancy. Not worth the price.

Reviewed on Dec 10, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Feb 12 - Feb 16

4 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Coach

Chicago (ORD) to Boston (BOS)

American Airlines • Coach
Save 100% on your flight
Price was $1,329, price is now $899 per person
$899
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 Cicero from Boston

Route Information for Flights from Boston to Cicero

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

Boston to Cicero

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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.