$51 Cheap flight deals from Boston (BOS) to Calumet City (CHI)

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This Weekend's Flight Deals from Boston to Calumet City

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.

Fri, Jan 9 - Wed, Jan 14
BOS
Logan Intl.
RFD
Greater Rockford
$142 Roundtrip, found 6 days ago
$142
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Jan 9 from Logan Intl. to Greater Rockford, returning Wed, Jan 14, priced at $142 found 6 days ago
Sun, Jan 11 - Thu, Jan 15
BOS
Logan Intl.
ORD
O'Hare Intl.
$175 Roundtrip, just found
$175
Roundtrip
just found
Select United flight, departing Sun, Jan 11 from Logan Intl. to O'Hare Intl., returning Thu, Jan 15, priced at $175 just found
Sat, Jan 10 - Sun, Jan 11
BOS
Logan Intl.
MDW
Midway Intl.
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jan 10 from Logan Intl. to Midway Intl., returning Sun, Jan 11, priced at $178 found 1 day ago
Sat, Jan 10 - Sat, Jan 24
MHT
Manchester-Boston Regional
ORD
O'Hare Intl.
$448 Roundtrip, found 3 days ago
$448
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jan 10 from Manchester-Boston Regional to O'Hare Intl., returning Sat, Jan 24, priced at $448 found 3 days ago

Airfares from $51 One Way, $105 Round Trip from Boston to Calumet City

Prices starting at $105 for return flights and $51 for one-way flights to Calumet City were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Feb 4 - Thu, Feb 5
BOS
Boston
ORD
Chicago
$105 Roundtrip, found 3 hours ago
$105
Roundtrip
found 3 hours ago
Select United flight, departing Wed, Feb 4 from Boston to Chicago, returning Thu, Feb 5, priced at $105 found 3 hours ago
Wed, Feb 4 - Thu, Feb 5
BOS
Boston
ORD
Chicago
$105 Roundtrip, found 3 hours ago
$105
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Feb 4 from Boston to Chicago, returning Thu, Feb 5, priced at $105 found 3 hours ago
Thu, Jan 22 - Mon, Jan 26
BOS
Boston
MDW
Chicago
$111 Roundtrip, just found
$111
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Jan 22 from Boston to Chicago, returning Mon, Jan 26, priced at $111 just found
Wed, Apr 29 - Sat, May 2
BOS
Boston
RFD
Rockford
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Apr 29 from Boston to Rockford, returning Sat, May 2, priced at $139 found 4 days ago
Thu, Apr 23 - Fri, Apr 24
ORH
Worcester
ORD
Chicago
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Apr 23 from Worcester to Chicago, returning Fri, Apr 24, priced at $155 found 1 day ago

Calumet City 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 10 - Feb 15

5 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $801, price is now $450 per person
$450
per person
found 6 hours 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

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (380 reviews)

Feb 10 - Feb 15

5 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,055, price is now $585 per person
$585
per person
found 6 hours ago
We always love staying here. Such great service and nice accommodations.

Reviewed on Nov 20, 2025

The Emily Hotel
4.0-star property

The Emily Hotel

9.2/10 Wonderful! (1,264 reviews)

Feb 10 - Feb 15

5 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $878, price is now $504 per person
$504
per person
found 6 hours ago
Cute and trendy hotwl but there was a loud party on-site which ruined experience. It felt clean but our mini fridge had takeout left from former guest, so maid service obviously missed that.

Reviewed on Jul 26, 2025

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More About Flying To Calumet City from Boston

Route Information for Flights from Boston to Calumet City

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

Boston to Calumet City

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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.