$59 Cheap flight deals from Boston (BOS) to Oak Park (CHI)

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This Weekend's Flight Deals from Boston to Oak Park

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.

Sun, Jan 18 - Sat, Jan 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$137 Roundtrip, just found
$137
Roundtrip
just found
Select United flight, departing Sun, Jan 18 from Logan Intl. to O'Hare Intl., returning Sat, Jan 24, priced at $137 just found
Sat, Jan 17 - Tue, Jan 20
BOS
Logan Intl.
RFD
Greater Rockford
$141 Roundtrip, found 4 days ago
$141
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jan 17 from Logan Intl. to Greater Rockford, returning Tue, Jan 20, priced at $141 found 4 days ago
Sun, Jan 18 - Sat, Jan 24
BOS
Logan Intl.
MDW
Midway Intl.
$144 Roundtrip, just found
$144
Roundtrip
just found
Select Southwest Airlines flight, departing Sun, Jan 18 from Logan Intl. to Midway Intl., returning Sat, Jan 24, priced at $144 just found
Fri, Jan 16 - Sat, Jan 17
PVD
T.F. Green
MDW
Midway Intl.
$769 Roundtrip, found 1 day ago
$769
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Jan 16 from T.F. Green to Midway Intl., returning Sat, Jan 17, priced at $769 found 1 day ago

Airfares from $59 One Way, $105 Round Trip from Boston to Oak Park

Prices starting at $105 for return flights and $59 for one-way flights to Oak Park were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Feb 9 - Wed, Feb 11
BOS
Boston
MDW
Chicago
$105 Roundtrip, found 4 days ago
$105
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Feb 9 from Boston to Chicago, returning Wed, Feb 11, priced at $105 found 4 days ago
Mon, Apr 27 - Wed, Apr 29
BOS
Boston
RFD
Rockford
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Apr 27 from Boston to Rockford, returning Wed, Apr 29, priced at $139 found 2 days ago
Thu, Feb 19 - Mon, Feb 23
ORH
Worcester
ORD
Chicago
$174 Roundtrip, found 3 days ago
$174
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Feb 19 from Worcester to Chicago, returning Mon, Feb 23, priced at $174 found 3 days ago
Mon, May 4 - Tue, May 12
PVD
Providence
ORD
Chicago
$187 Roundtrip, found 2 days ago
$187
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, May 4 from Providence to Chicago, returning Tue, May 12, priced at $187 found 2 days ago
Thu, Feb 12 - Mon, Feb 16
PVD
Providence
MDW
Chicago
$222 Roundtrip, found 3 days ago
$222
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Feb 12 from Providence to Chicago, returning Mon, Feb 16, priced at $222 found 3 days ago

Oak Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Destination Geneva National
4.0-star property

Destination Geneva National

9/10 Wonderful! (451 reviews)

Feb 12 - Feb 16

4 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Price was $524, price is now $378 per person
$378
per person
found 21 hours ago
It was a beautiful property and I will certainly be back.

Reviewed on Feb 27, 2025

La Banque Hotel
4.0-star property

La Banque Hotel

9.4/10 Exceptional! (447 reviews)

Feb 12 - Feb 16

4 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $844, price is now $539 per person
$539
per person
found 21 hours ago
Beautiful boutique hotel with great staff!

Reviewed on Sep 16, 2022

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Mar 11 - Mar 13

2 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $699, price is now $492 per person
$492
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

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Oak Park packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG
3.0-star property

Holiday Inn Chicago O'Hare – Rosemont by IHG

9/10 Wonderful! (2,591 reviews)

Feb 20 - Feb 23

3 night stay

Boston (BOS) to Chicago (ORD)

Delta • PremiumEconomy

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy
Price was $632, price is now $516 per person
$516
per person
found 12 hours ago
Very nice staff. Clean room, and nice restaurant and coffee bar in the lobby. I have stayed there several times. It's a convinient location as well.

Reviewed on Dec 29, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 20 - Feb 23

3 night stay

Boston (BOS) to Chicago (ORD)

Delta • PremiumEconomy

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy
Price was $889, price is now $589 per person
$589
per person
found 12 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

Hilton Rosemont Chicago O'Hare
3.5-star property

Hilton Rosemont Chicago O'Hare

8.4/10 Very Good! (1,000 reviews)

Feb 20 - Feb 23

3 night stay

Boston (BOS) to Chicago (ORD)

Delta • PremiumEconomy

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy
Price was $701, price is now $583 per person
$583
per person
found 12 hours ago
Good hotel close to airport, with free airport shuttle, 7-10 min away. Quite convenient

Reviewed on Nov 4, 2025

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More About Flying To Oak Park from Boston

Route Information for Flights from Boston to Oak Park

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

Boston to Oak Park

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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.