$50 Cheap flight deals from Boston (BOS) to Romeoville (CHI)

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This Weekend's Flight Deals from Boston to Romeoville

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 2 - Mon, Jan 5
BOS
Logan Intl.
RFD
Greater Rockford
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Jan 2 from Logan Intl. to Greater Rockford, returning Mon, Jan 5, priced at $160 found 2 days ago
Sun, Jan 4 - Mon, Jan 5
BOS
Logan Intl.
MDW
Midway Intl.
$221 Roundtrip, found 9 hours ago
$221
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Sun, Jan 4 from Logan Intl. to Midway Intl., returning Mon, Jan 5, priced at $221 found 9 hours ago
Sun, Jan 4 - Mon, Jan 5
BOS
Logan Intl.
ORD
O'Hare Intl.
$243 Roundtrip, found 9 hours ago
$243
Roundtrip
found 9 hours ago
Select United flight, departing Sun, Jan 4 from Logan Intl. to O'Hare Intl., returning Mon, Jan 5, priced at $243 found 9 hours ago
Sun, Jan 4 - Tue, Jan 20
PVD
T.F. Green
ORD
O'Hare Intl.
$464 Roundtrip, found 1 day ago
$464
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Jan 4 from T.F. Green to O'Hare Intl., returning Tue, Jan 20, priced at $464 found 1 day ago

Airfares from $50 One Way, $111 Round Trip from Boston to Romeoville

Prices starting at $111 for return flights and $50 for one-way flights to Romeoville were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jan 24 - Sun, Jan 25
BOS
Boston
MDW
Chicago
$111 Roundtrip, found 1 day ago
$111
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jan 24 from Boston to Chicago, returning Sun, Jan 25, priced at $111 found 1 day ago
Wed, Feb 4 - Sat, Feb 7
BOS
Boston
ORD
Chicago
$117 Roundtrip, found 4 hours ago
$117
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Feb 4 from Boston to Chicago, returning Sat, Feb 7, priced at $117 found 4 hours ago
Wed, Feb 4 - Sat, Feb 7
BOS
Boston
ORD
Chicago
$117 Roundtrip, found 4 hours ago
$117
Roundtrip
found 4 hours ago
Select United flight, departing Wed, Feb 4 from Boston to Chicago, returning Sat, Feb 7, priced at $117 found 4 hours ago
Wed, Feb 4 - Sat, Feb 7
BOS
Boston
ORD
Chicago
$117 Roundtrip, found 4 hours ago
$117
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, Feb 4 from Boston to Chicago, returning Sat, Feb 7, priced at $117 found 4 hours ago
Wed, Feb 4 - Sat, Feb 7
BOS
Boston
RFD
Rockford
$139 Roundtrip, found 4 hours ago
$139
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Feb 4 from Boston to Rockford, returning Sat, Feb 7, priced at $139 found 4 hours ago

Romeoville economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago Downtown
4.0-star property

The Royal Sonesta Chicago Downtown

9.4/10 Exceptional! (3,062 reviews)

Feb 20 - Feb 23

3 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • Coach
Price was $391, price is now $279 per person
$279
per person
found 24 hours ago
The lady who checked us in (the countess) was very friendly and welcoming. Even though she was the only person working the front desk, she did not get frazzled or curt. She was great! Room was beautiful and had an amazing view!

Reviewed on Dec 22, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 20 - Feb 22

2 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Coach

Chicago (ORD) to Boston (BOS)

Southwest Airlines • Coach
Price was $436, price is now $332 per person
$332
per person
found 24 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

Chicago Athletic Association, a Hyatt Hotel
4.5-star property

Chicago Athletic Association, a Hyatt Hotel

9/10 Wonderful! (1,002 reviews)

Feb 20 - Feb 23

3 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • Coach
Price was $427, price is now $333 per person
$333
per person
found 24 hours ago
The location couldn’t be better—right across from The Bean. The hotel is gorgeous, old-style elegance with a beautiful, antique-like bar, a cozy fireplace, and fabulous wooden details throughout. The food and drinks were excellent. The service was outstanding and attentive, from the bellman to the janitorial staff. The rooms are spacious, with a very comfortable large king bed. Overall, a great experience. I highly recommend it!

Reviewed on Dec 24, 2025

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More About Flying To Romeoville from Boston

Route Information for Flights from Boston to Romeoville

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

Boston to Romeoville

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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.