$75 Cheap flight deals from Boston (BOS) to Calumet City (CHI)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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, Jul 3 - Sun, Jul 5
BOS
Logan Intl.
MDW
Midway Intl.
$277 Roundtrip, found 4 hours ago
$277
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Fri, Jul 3 from Logan Intl. to Midway Intl., returning Sun, Jul 5, priced at $277 found 4 hours ago
Fri, Jul 3 - Mon, Jul 6
BOS
Logan Intl.
ORD
O'Hare Intl.
$283 Roundtrip, found 3 hours ago
$283
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Fri, Jul 3 from Logan Intl. to O'Hare Intl., returning Mon, Jul 6, priced at $283 found 3 hours ago
Fri, Jul 3 - Sun, Jul 5
BOS
Logan Intl.
RFD
Greater Rockford
$332 Roundtrip, found 19 hours ago
$332
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Fri, Jul 3 from Logan Intl. to Greater Rockford, returning Sun, Jul 5, priced at $332 found 19 hours ago
Sun, Jul 5 - Sun, Jul 12
PVD
T.F. Green
MDW
Midway Intl.
$485 Roundtrip, found 6 days ago
$485
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Jul 5 from T.F. Green to Midway Intl., returning Sun, Jul 12, priced at $485 found 6 days ago

Airfares from $75 One Way, $149 Round Trip from Boston to Calumet City

Prices starting at $149 for return flights and $75 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, Aug 26 - Tue, Sep 1
BOS
Boston
MDW
Chicago
$149 Roundtrip, found 4 days ago
$149
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Aug 26 from Boston to Chicago, returning Tue, Sep 1, priced at $149 found 4 days ago
Wed, Aug 26 - Tue, Sep 1
BOS
Boston
ORD
Chicago
$150 Roundtrip, found 1 day ago
$150
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 26 from Boston to Chicago, returning Tue, Sep 1, priced at $150 found 1 day ago
Thu, Jul 30 - Mon, Aug 3
ORH
Worcester
ORD
Chicago
$205 Roundtrip, found 1 day ago
$205
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jul 30 from Worcester to Chicago, returning Mon, Aug 3, priced at $205 found 1 day ago
Tue, Sep 22 - Tue, Sep 29
PVD
Providence
ORD
Chicago
$218 Roundtrip, found 5 days ago
$218
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Sep 22 from Providence to Chicago, returning Tue, Sep 29, priced at $218 found 5 days ago
Sat, Oct 10 - Tue, Oct 13
PVD
Providence
MDW
Chicago
$245 Roundtrip, found 1 day ago
$245
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Oct 10 from Providence to Chicago, returning Tue, Oct 13, priced at $245 found 1 day ago

Calumet City economy flight packages

Price found within the past 48 hours. Click for updated prices.
Saratoga Motel By Capital O Near Midway Airport Chicago IL
2.5-star property

Saratoga Motel By Capital O Near Midway Airport Chicago IL

6/10 (66 reviews)

Jul 28 - Aug 4

7 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,115, price is now $728 per person
$728
per person
found 11 hours ago
The Willows Hotel
3.0-star property

The Willows Hotel

8.6/10 Excellent! (1,005 reviews)

Jul 28 - Aug 4

7 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,910, price is now $1,320 per person
$1,320
per person
found 11 hours ago
Awesome in all areas,,,ESPECIALLY in office staff.

Reviewed on Oct 27, 2025

Holiday Inn Chicago – Midway Airport S by IHG
2.5-star property

Holiday Inn Chicago – Midway Airport S by IHG

8.2/10 Very Good! (1,035 reviews)

Jul 28 - Aug 4

7 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,090, price is now $764 per person
$764
per person
found 11 hours ago
The room was clean & comfortable. However the breakfast that I prepaid for was not worth the money. We arrived when it started which was 7:30 am which I consider late for most hotels. It was inconvenient based on our plans, and nowhere on this app did it say the breakfast times. I should’ve done more research to find that part out. Then the food wasn’t even ready for us to eat from the buffet. They were slowly bringing out food. There were only four people in the dining area, but when we went up to get food they had already ran out of bacon. They kept saying the eggs were on their way, but they didn’t even get set out until after 7:50 am which is when we left because we had to be at an event at 8 am. The staff was friendly, but definitely not prepared for the 7:30 start time. Again, not worth the money. I regret prepaying for breakfast as I only ended up eating a yogurt with some fruit.

Reviewed on Jan 25, 2026

Don't see what you're looking for?
See all available trips from Boston to Calumet City
View all trips

Calumet City packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Chicago/Aurora
2.5-star property

Hampton Inn & Suites Chicago/Aurora

9.2/10 Wonderful! (1,010 reviews)

Aug 8 - Aug 10

2 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $680, price is now $649 per person
$649
per person
found 15 hours ago
The pool was worth it for the kids. Nice amenities, decent breakfast. Nice size suite and was clean. Staff was also friendly and helpful. I will absolutely stay again!!!!

Reviewed on Jan 26, 2025

Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

9/10 Wonderful! (3,648 reviews)

Aug 8 - Aug 10

2 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $856, price is now $727 per person
$727
per person
found 15 hours ago
This property is a central location to just about everything. I was able to walk to majority of my destinations.

Reviewed on Mar 10, 2026

Hilton Chicago/Magnificent Mile Suites
3.5-star property

Hilton Chicago/Magnificent Mile Suites

9/10 Wonderful! (4,466 reviews)

Aug 8 - Aug 10

2 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $830, price is now $747 per person
$747
per person
found 15 hours ago
Great stay. Great location.

Reviewed on Mar 23, 2026

Don't see what you're looking for?
See all available trips from Boston to Calumet City
View all trips

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

Rack up your savings with low-cost flights from Boston to Calumet City with Orbitz On-the-Go. Orbitz On-the-Go offers mobile-only deals and cutting edge mobile tools to help you find bargain flights from Boston to Calumet City.

Mobile-Only Deals on Boston to Calumet City flights

Find guaranteed low prices on Boston to Calumet City flights using Orbitz On-the-Go. You can book discount domestic flights from Boston to Calumet City, and international tickets on Boston to Calumet City flights using our mobile site and apps.

Free Alerts Are No Surprise

Not only will you find cheap tickets on flights from Boston to Calumet City, but Orbitz free alerts will keep you up to speed on flight status, plus gate and baggage claim details. Receive instant updates via your choice of email, voice or text. Orbitz keeps you easily on task and on budget.

Share Itineraries on Flights from Boston to Calumet City

Are you traveling for business, pleasure or a combination of both? Keep family, friends and business contacts posted on flight and gate info. Just use MyTrips for iPhone, Android and web phones like Blackberry and Windows.

Add Smiles to Your Miles with Sales and Deals on Boston to Calumet City Flights

Travel planning is easy when you store your frequent flyer and loyalty program information on your Orbitz account. Then snag a low-fare air ticket on Boston to Calumet City flights, and you’re done. No muss, no fuss. Your miles will fly by with Orbitz On-the-Go cutting edge mobile tools and guaranteed low prices.

More Destinations

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.