$90 Cheap flight deals from Boston (BOS) to Arlington Heights (CHI)
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This Weekend's Flight Deals from Boston to Arlington Heights
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.
BOS
Logan Intl.
MDW
Midway Intl.
$311 Roundtrip, found 1 day ago
$311
Roundtrip
found 1 day ago
BOS
Logan Intl.
ORD
O'Hare Intl.
$322 Roundtrip, found 18 hours ago
$322
Roundtrip
found 18 hours ago
ORH
Worcester Regional
ORD
O'Hare Intl.
$326 Roundtrip, found 6 hours ago
$326
Roundtrip
found 6 hours ago
PVD
T.F. Green
ORD
O'Hare Intl.
$411 Roundtrip, found 5 days ago
$411
Roundtrip
found 5 days ago
Airfares from $90 One Way, $198 Round Trip from Boston to Arlington Heights
Prices starting at $198 for return flights and $90 for one-way flights to Arlington Heights were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
BOS
Boston
ORD
Chicago
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
BOS
Boston
RFD
Rockford
$216 Roundtrip, found 1 day ago
$216
Roundtrip
found 1 day ago
BOS
Boston
MDW
Chicago
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
ORH
Worcester
ORD
Chicago
$232 Roundtrip, found 2 days ago
$232
Roundtrip
found 2 days ago
PVD
Providence
ORD
Chicago
$257 Roundtrip, found 3 days ago
$257
Roundtrip
found 3 days ago
Arlington Heights economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Saint Clair- Magnificent Mile
8.4/10 Very Good! (2,146 reviews)
Oct 22 - Oct 26
4 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
Price was $936, price is now $618 per person
$618
per person
found 1 day ago
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (5,045 reviews)
Oct 22 - Oct 26
4 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
Price was $1,488, price is now $965 per person
$965
per person
found 1 day ago
Room was ok, didn’t get the view I requested.
Some of the reception people was rude. Breakfast was adequate. No omellete bar,
Reviewed on Aug 29, 2026
4.5-star property
Swissotel - Chicago
9/10 Wonderful! (3,553 reviews)
Oct 22 - Oct 26
4 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
Price was $1,303, price is now $876 per person
$876
per person
found 1 day ago
My sister and I came to Chicago from Baltimore to see the Obama Presidential Center. When I researched hotels to stay at in Chicago I was very impressed with Swissotel ratings. I could’ve made a better choice. We didn’t get to see everything we wanted to see, but when we do come back to Chicago Swissotel is definitely where we’ll be staying. So if you’re planning on coming to Chicago Swissotel is the best choice.
Reviewed on Aug 29, 2026
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View all tripsArlington Heights first class flight packages
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Quality Inn Sawyer
7.4/10 Good! (1,012 reviews)
Oct 7 - Oct 11
4 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Non-stop roundtrip • FirstClass
Price was $879, price is now $874 per person
$874
per person
found 22 hours ago
The room had a terrible smell. Switched rooms and smelled little less horrible than the first. My nose was plugged the next morning. Breakfast was a 2/5.
We stopped over to sleep during our road trip, it was good enough for that.
Reviewed on Aug 29, 2026
2.5-star property
Holiday Inn Express Hotel & Suites Niles by IHG
9/10 Wonderful! (796 reviews)
Oct 7 - Oct 11
4 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Non-stop roundtrip • FirstClass
Price was $1,475, price is now $1,457 per person
$1,457
per person
found 22 hours ago
Had to ask for room change after finding bugs in bathroom and hair in bed as well as dirt around the room. 2nd room was better. Room was on first floor which can be noisy but breakfast was nice and so was staff.
Reviewed on Aug 29, 2026
Don't see what you're looking for?
See all available trips from Boston to Arlington Heights
View all tripsMore About Flying To Arlington Heights from Boston
Route Information for Flights from Boston to Arlington Heights
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Arlington Heights
If it is not enough that we have guaranteed low prices for Boston to Arlington Heights flights, Orbitz can also integrate your hotel and car rental needs into the package. This ensures your trip goes smoothly and you get the best possible bargain.
Save Big On Hotels With Our Summer Hotel Sale When Booking Boston to Arlington Heights Flights
We will get you bargain air tickets for Boston to Arlington Heights flights and can save you even more with our Summer Hotel sale. You can get a discount of up to 40% when you book a hotel along with your bargain flight from Orbitz.
If You Are Going To The Beach We Can Save You Even More
When you are arranging budget flights from Boston to Arlington Heights, you can save even more by staying near a beach. Orbitz Beach Hotel Deals will allow you to get as much as half off the price of an already cheap hotel. Saving money has never been this fun.
Plan A Spontaneous Trip Using Our Top Hotel and Flight Destinations
Want to know where other people are staying after flights from Boston to Arlington Heights? We not only recommend top destinations, but will tell you the most popular places to stay after {origin.name} to Arlington Heights flights.
Use Orbitz.com For Up To The Minute Hot Deals
Budget deals on flights from Boston to Arlington Heights are constantly changing. You can get up-to-the-minute updates on the hottest deals on discount tickets and hotels on our website.
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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.