$90 Cheap flight deals from Boston (BOS) to Rosemont (CHI)
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This Weekend's Flight Deals from Boston to Rosemont
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 23 hours ago
$311
Roundtrip
found 23 hours ago
BOS
Logan Intl.
ORD
O'Hare Intl.
$322 Roundtrip, just found
$322
Roundtrip
just found
ORH
Worcester Regional
ORD
O'Hare Intl.
$326 Roundtrip, found 23 hours ago
$326
Roundtrip
found 23 hours ago
PVD
T.F. Green
ORD
O'Hare Intl.
$475 Roundtrip, just found
$475
Roundtrip
just found
Airfares from $90 One Way, $199 Round Trip from Boston to Rosemont
Prices starting at $199 for return flights and $90 for one-way flights to Rosemont 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
$199 Roundtrip, found 4 days ago
$199
Roundtrip
found 4 days ago
BOS
Boston
RFD
Rockford
$216 Roundtrip, found 4 days ago
$216
Roundtrip
found 4 days ago
BOS
Boston
MDW
Chicago
$217 Roundtrip, found 3 hours ago
$217
Roundtrip
found 3 hours ago
PVD
Providence
MDW
Chicago
$261 Roundtrip, found 5 days ago
$261
Roundtrip
found 5 days ago
PVD
Providence
ORD
Chicago
$261 Roundtrip, found 5 days ago
$261
Roundtrip
found 5 days ago
Rosemont economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (5,106 reviews)
Oct 22 - Oct 24
2 night stay
Boston (BOS) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $946, price is now $672 per person
$672
per person
found 1 day ago
Clean and nice location
Reviewed on Sep 1, 2026
4.0-star property
Renaissance Chicago Downtown Hotel
9.2/10 Wonderful! (1,009 reviews)
Oct 22 - Oct 24
2 night stay
Boston (BOS) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,073, price is now $742 per person
$742
per person
found 1 day ago
The hotel itself was nice, but communication and a few amenities were disappointing.
I booked through Hotels.com and was told I would pay a $120 destination fee at the property. At check-in, I specifically asked what the destination package included and was told we received complimentary drinks, $15 bar vouchers, and other amenities. Later, after noticing an additional charge on my card, I was given different information about what was actually included.
I was also told after the fact that Garrett Popcorn was included and that it was listed on a card given at check-in. No one explained this to us, so we never received it. If guests are paying a mandatory destination fee, staff should clearly explain what is included and how to redeem it.
The rooftop bar was one of the main things we were excited about, but it doesn’t open until 4 p.m., so lunch wasn’t an option. It also filled up quickly, and hotel guests don’t receive priority seating.
Lastly, most food options close around midnight, and there are no vending machines or convenient late-night options. There is a 7-Eleven within walking distance, but the area felt a little sketchy late at night.
Overall, a nice hotel, but better communication and more consideration for hotel guests would improve the experience.
Reviewed on Aug 28, 2026
3.5-star property
The Chicago Hotel Collection - Wrigleyville
7.2/10 Good! (1,023 reviews)
Oct 21 - Oct 24
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
American Airlines • Coach
Save 100% on your flight
Price was $1,182, price is now $879 per person
$879
per person
found 1 day ago
The "virtual" front desk was terrible. They were hard to reach, we called & called, left messages, and texted. The person from housekeeping who (finally) showed up to let us in to stow are bags did not speak english. We had to reach the virtual front desk again to pick up the bags, and again the experience was not pleasant. They were singularly unhelpful as we tried to figure out their system.
The elevator broke. The door to our room would not lock. In the lobby the phone rings and rings with no one there to answer it. The common bathroom for the hotel is in a dark, serpentine hallway in the basement.
As we were preparing to leave on Sunday, we had to witness yet another couple outside on the street trying to get ahold of someone and getting as frustrated as we had been.
At Pilot Project Brewery next door, one of the wait staff told us that no one who comes there has anything good to say about this hotel. I concur.
Reviewed on Sep 1, 2026
Rosemont first class flight packages
Price found within the past 48 hours. Click for updated prices.
5.0-star property
Trump International Hotel & Tower Chicago
9.6/10 Exceptional! (2,003 reviews)
Oct 16 - Oct 18
2 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Roundtrip • FirstClass
Price was $1,452, price is now $1,186 per person
$1,186
per person
found 1 day ago
Pablo was amazing and he made my 50th birthday experience amazing . Thank you for the champagne and cake surprise . Super recommended .
Reviewed on Sep 1, 2026
More About Flying To Rosemont from Boston
Route Information for Flights from Boston to Rosemont
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Rosemont
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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.