$88 Cheap flight deals from Boston (BOS) to Skokie (CHI)

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This Weekend's Flight Deals from Boston to Skokie

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.

Sat, Aug 15 - Tue, Aug 18
BOS
Logan Intl.
RFD
Greater Rockford
$299 Roundtrip, found 5 days ago
$299
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 15 from Logan Intl. to Greater Rockford, returning Tue, Aug 18, priced at $299 found 5 days ago
Fri, Aug 14 - Mon, Aug 17
BOS
Logan Intl.
MDW
Midway Intl.
$321 Roundtrip, found 14 hours ago
$321
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Fri, Aug 14 from Logan Intl. to Midway Intl., returning Mon, Aug 17, priced at $321 found 14 hours ago
Fri, Aug 14 - Mon, Aug 17
BOS
Logan Intl.
ORD
O'Hare Intl.
$372 Roundtrip, just found
$372
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, Aug 14 from Logan Intl. to O'Hare Intl., returning Mon, Aug 17, priced at $372 just found
Sun, Aug 16 - Mon, Aug 17
PVD
T.F. Green
ORD
O'Hare Intl.
$571 Roundtrip, found 14 hours ago
$571
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Sun, Aug 16 from T.F. Green to O'Hare Intl., returning Mon, Aug 17, priced at $571 found 14 hours ago

Airfares from $88 One Way, $186 Round Trip from Boston to Skokie

Prices starting at $186 for return flights and $88 for one-way flights to Skokie were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Aug 25 - Wed, Sep 2
BOS
Boston
ORD
Chicago
$186 Roundtrip, found 10 hours ago
$186
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Boston to Chicago, returning Wed, Sep 2, priced at $186 found 10 hours ago
Sat, Oct 3 - Tue, Oct 6
BOS
Boston
MDW
Chicago
$205 Roundtrip, found 14 hours ago
$205
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, Oct 3 from Boston to Chicago, returning Tue, Oct 6, priced at $205 found 14 hours ago
Sat, Sep 5 - Sun, Sep 6
PVD
Providence
MDW
Chicago
$228 Roundtrip, found 14 hours ago
$228
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Providence to Chicago, returning Sun, Sep 6, priced at $228 found 14 hours ago
Sat, Sep 5 - Sun, Sep 6
PVD
Providence
ORD
Chicago
$228 Roundtrip, found 14 hours ago
$228
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sat, Sep 5 from Providence to Chicago, returning Sun, Sep 6, priced at $228 found 14 hours ago
Fri, Sep 4 - Wed, Sep 9
BOS
Boston
RFD
Rockford
$230 Roundtrip, found 1 day ago
$230
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Sep 4 from Boston to Rockford, returning Wed, Sep 9, priced at $230 found 1 day ago

Skokie economy flight packages

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

8.8/10 Excellent! (2,293 reviews)

Sep 22 - Sep 24

2 night stay

Boston (BOS) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Non-stop • Coach
Price was $754, price is now $586 per person
$586
per person
found 1 day ago

Level Chicago - River North
4.0-star property

Level Chicago - River North

9.2/10 Wonderful! (1,041 reviews)

Sep 10 - Sep 14

4 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,557, price is now $956 per person
$956
per person
found 1 day ago
The only thing that was negative was it took forever to check in and limited parking by the lobby entrance.

Reviewed on Aug 7, 2026

The Godfrey Hotel Chicago
4.5-star property

The Godfrey Hotel Chicago

8.8/10 Excellent! (2,360 reviews)

Sep 10 - Sep 14

4 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,283, price is now $998 per person
$998
per person
found 1 day ago
A total disappointment for birthday week. The staff is rude, unfriendly and very unhelpful. The best employees were the cleaning staff. I sent several emails prior to checking in about down pillows needing removed, they didn’t comply, caused an asthma attack, acted like I was a bother when I called asking for the pillows to be replaced and the gentleman who brought them brought 2 foam and 2 more down, all out of pillowcases. I asked to speak to a manager twice, never got to. We had a suite and it is not worth the hype, blocked views and the wallpaper was all scuffed up. In a city like Chicago you have many choices, you can choose better.

Reviewed on Aug 7, 2026

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Skokie packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,512 reviews)

Sep 18 - Sep 21

3 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,407, price is now $1,022 per person
$1,022
per person
found 24 hours ago

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (4,907 reviews)

Sep 18 - Sep 21

3 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,760, price is now $1,298 per person
$1,298
per person
found 24 hours ago
Outstanding place in Streeterville

Reviewed on Aug 8, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,631 reviews)

Sep 18 - Sep 21

3 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,483, price is now $1,113 per person
$1,113
per person
found 24 hours ago
Traveled with my partner, it felt romantic and we loved the view and all the nearby attractions. We were given a $10 credit to the restaurant but didn’t use them because we were too busy exploring the entire pier. There is no pool however the oak beach is nearby. The property felt safe although it was accessible to everyone, you had to use your room key to access the elevators. The pier closed at 10p to public so we had private access to the beautiful nighttime views. Make sure you wear walking shoes!! The only things that bothered us were, Stains on the floor and bench in our room, shower head had weak water flow, other than that it was an amazing stay!!! Definitely will be back with my children.

Reviewed on Aug 8, 2026

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More About Flying To Skokie from Boston

Route Information for Flights from Boston to Skokie

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

Boston to Skokie

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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.