$100 Cheap flight deals from Boston (BOS) to Schaumburg (CHI)
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This Weekend's Flight Deals from Boston to Schaumburg
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.
$297 Roundtrip, found 3 days ago
$297
Roundtrip
found 3 days ago
BOS
Logan Intl.
ORD
O'Hare Intl.
$357 Roundtrip, found 9 hours ago
$357
Roundtrip
found 9 hours ago
PVD
T.F. Green
ORD
O'Hare Intl.
$436 Roundtrip, found 9 hours ago
$436
Roundtrip
found 9 hours ago
Airfares from $100 One Way, $227 Round Trip from Boston to Schaumburg
Prices starting at $227 for return flights and $100 for one-way flights to Schaumburg 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
$227 Roundtrip, found 21 hours ago
$227
Roundtrip
found 21 hours ago
BOS
Boston
MDW
Chicago
$230 Roundtrip, found 4 days ago
$230
Roundtrip
found 4 days ago
BOS
Boston
ORD
Chicago
$247 Roundtrip, just found
$247
Roundtrip
just found
BOS
Boston
ORD
Chicago
$280 Roundtrip, found 7 hours ago
$280
Roundtrip
found 7 hours ago
BOS
Boston
MDW
Chicago
$291 Roundtrip, found 6 hours ago
$291
Roundtrip
found 6 hours ago
Schaumburg economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago Fulton Market
9.2/10 Wonderful! (591 reviews)
Dec 30 - Jan 3
4 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
Delta • Coach
Price was $974, price is now $739 per person
$739
per person
found 1 day ago
If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa.
There was no housekeeping.
Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before you arrive!
There is no lobby, no where in the hotel to hang, no vibe. You are literally staying in a condo and have to exit the building and walk a few blocks to be anywhere. Maybe this is the new hotel experience, but for me, I still like some ammenities.
The room was fine
T
Reviewed on Nov 4, 2026
5.0-star property
Trump International Hotel & Tower Chicago
9.6/10 Exceptional! (2,057 reviews)
Dec 30 - Jan 4
5 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Price was $2,180, price is now $1,638 per person
$1,638
per person
found 1 day ago
Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint
Reviewed on Nov 6, 2026
5.0-star property
Park Hyatt Chicago
9.6/10 Exceptional! (1,002 reviews)
Dec 30 - Jan 4
5 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Price was $2,108, price is now $1,605 per person
$1,605
per person
found 1 day ago
Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott.
For example, there was a hair in the bed. When we reported it, the hotel changed the sheets and asked if we wanted to switch rooms, but no apology or other compensation was offered.
The service was fine but incredibly slow, which we experienced with three different requests. Two were for the same bath salts, which are already provided in the room, so it wasn’t a special request. We had to call twice, and they arrived after 45 to 55 minutes. For the third, I went down to the front desk to ask for a printer, and they offered to print the documents and send them to my room. After 45 minutes, I went back down, and it turned out they had completely forgotten about the request, so I had them printed right there.
The pool was dirty. On three different occasions over two days, there were toys left in the pool even after the people using them were already gone. The fruit in the gym was also old and had gone bad.
Reviewed on Nov 4, 2026
Schaumburg first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Eurostars Magnificent Mile
9/10 Wonderful! (3,962 reviews)
Dec 7 - Dec 11
4 night stay
Boston (BOS) to Chicago (ORD)
Delta • Non-stop roundtrip • FirstClass
Price was $978, price is now $795 per person
$795
per person
found 1 day ago
Excelente ubicación, habitaciones amplias, limpias y muy cómodas. Teníamos una vista extraordinaria de la ciudad .
Reviewed on Nov 5, 2026
More About Flying To Schaumburg from Boston
Route Information for Flights from Boston to Schaumburg
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Schaumburg
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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.