$51 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.

Fri, Jan 9 - Tue, Jan 13
BOS
Logan Intl.
ORD
O'Hare Intl.
$126 Roundtrip, found 10 hours ago
$126
Roundtrip
found 10 hours ago
Select United flight, departing Fri, Jan 9 from Logan Intl. to O'Hare Intl., returning Tue, Jan 13, priced at $126 found 10 hours ago
Fri, Jan 9 - Sat, Jan 10
BOS
Logan Intl.
RFD
Greater Rockford
$142 Roundtrip, found 15 hours ago
$142
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Fri, Jan 9 from Logan Intl. to Greater Rockford, returning Sat, Jan 10, priced at $142 found 15 hours ago
Sun, Jan 11 - Mon, Jan 12
BOS
Logan Intl.
MDW
Midway Intl.
$192 Roundtrip, found 15 hours ago
$192
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Sun, Jan 11 from Logan Intl. to Midway Intl., returning Mon, Jan 12, priced at $192 found 15 hours ago
Sat, Jan 10 - Sat, Jan 24
MHT
Manchester-Boston Regional
ORD
O'Hare Intl.
$448 Roundtrip, found 4 days ago
$448
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jan 10 from Manchester-Boston Regional to O'Hare Intl., returning Sat, Jan 24, priced at $448 found 4 days ago

Airfares from $51 One Way, $105 Round Trip from Boston to Oak Park

Prices starting at $105 for return flights and $51 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 - Tue, Feb 10
BOS
Boston
MDW
Chicago
$105 Roundtrip, found 15 hours ago
$105
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Mon, Feb 9 from Boston to Chicago, returning Tue, Feb 10, priced at $105 found 15 hours ago
Thu, May 7 - Mon, May 11
BOS
Boston
ORD
Chicago
$105 Roundtrip, just found
$105
Roundtrip
just found
Select United flight, departing Thu, May 7 from Boston to Chicago, returning Mon, May 11, priced at $105 just found
Mon, Feb 9 - Tue, Feb 10
BOS
Boston
ORD
Chicago
$105 Roundtrip, found 15 hours ago
$105
Roundtrip
found 15 hours ago
Select Delta flight, departing Mon, Feb 9 from Boston to Chicago, returning Tue, Feb 10, priced at $105 found 15 hours ago
Wed, Apr 29 - Sat, May 2
BOS
Boston
RFD
Rockford
$139 Roundtrip, found 5 days ago
$139
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 29 from Boston to Rockford, returning Sat, May 2, priced at $139 found 5 days ago
Thu, Apr 23 - Fri, Apr 24
ORH
Worcester
ORD
Chicago
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Apr 23 from Worcester to Chicago, returning Fri, Apr 24, priced at $155 found 1 day ago

Oak Park 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 27 - Mar 2

3 night stay

Boston (BOS) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Boston (BOS)

Delta • Coach
Price was $387, price is now $273 per person
$273
per person
found 16 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

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (380 reviews)

Feb 12 - Feb 16

4 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Coach

Chicago (ORD) to Boston (BOS)

American Airlines • Coach
Save 100% on your flight
Price was $827, price is now $596 per person
$596
per person
found 10 hours ago
We always love staying here. Such great service and nice accommodations.

Reviewed on Nov 20, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 14 - Feb 16

2 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
Price was $482, price is now $354 per person
$354
per person
found 16 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

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Oak Park packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (2,008 reviews)

Feb 20 - Feb 22

2 night stay

Boston (BOS) to Chicago (ORD)

Delta • PremiumEconomy

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy
Price was $674, price is now $569 per person
$569
per person
found 2 hours ago
Solid place to stay

Reviewed on Nov 5, 2025

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,000 reviews)

Feb 20 - Feb 22

2 night stay

Boston (BOS) to Chicago (ORD)

Delta • PremiumEconomy

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy
Price was $1,245, price is now $1,011 per person
$1,011
per person
found 2 hours ago
Lovely room and spacious bathroom plus all of the high end touches (robes, slippers to soft mats and towels and great bath products and loved the nespresso maker!) View was not great but gym and lobby made up for it; bar was too crowded and we couldn’t get a late checkout but at least it was noon and they held our bags for a few hours!

Reviewed on Dec 31, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Feb 20 - Feb 22

2 night stay

Boston (BOS) to Chicago (ORD)

Delta • PremiumEconomy

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy
Price was $961, price is now $792 per person
$792
per person
found 2 hours 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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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.