$113 Cheap flight deals from Philadelphia (ILG) to Southern Wisconsin (CHI)

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This Weekend's Flight Deals from Philadelphia to Southern Wisconsin

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, May 30 - Sun, May 31
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$250 Roundtrip, found 20 hours ago
$250
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sat, May 30 from Philadelphia Intl. to General Mitchell Intl., returning Sun, May 31, priced at $250 found 20 hours ago
Fri, May 29 - Wed, Jun 3
PHL
Philadelphia Intl.
RFD
Greater Rockford
$356 Roundtrip, found 6 days ago
$356
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 29 from Philadelphia Intl. to Greater Rockford, returning Wed, Jun 3, priced at $356 found 6 days ago
Fri, May 29 - Wed, Jun 3
PHL
Philadelphia Intl.
MSN
Dane County Regional
$470 Roundtrip, found 4 days ago
$470
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, May 29 from Philadelphia Intl. to Dane County Regional, returning Wed, Jun 3, priced at $470 found 4 days ago
Fri, May 29 - Sun, May 31
ABE
Lehigh Valley Intl.
RFD
Greater Rockford
$491 Roundtrip, found 6 days ago
$491
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 29 from Lehigh Valley Intl. to Greater Rockford, returning Sun, May 31, priced at $491 found 6 days ago

Airfares from $113 One Way, $218 Round Trip from Philadelphia to Southern Wisconsin

Prices starting at $218 for return flights and $113 for one-way flights to Southern Wisconsin 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, Jul 11 - Sat, Jul 18
PHL
Philadelphia
MKE
Milwaukee
$218 Roundtrip, found 4 days ago
$218
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jul 11 from Philadelphia to Milwaukee, returning Sat, Jul 18, priced at $218 found 4 days ago
Sat, Jun 6 - Thu, Jun 11
TTN
Trenton
MKE
Milwaukee
$239 Roundtrip, found 6 days ago
$239
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Trenton to Milwaukee, returning Thu, Jun 11, priced at $239 found 6 days ago
Sat, Aug 8 - Wed, Aug 12
PHL
Philadelphia
RFD
Rockford
$246 Roundtrip, found 15 hours ago
$246
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Sat, Aug 8 from Philadelphia to Rockford, returning Wed, Aug 12, priced at $246 found 15 hours ago
Thu, Aug 27 - Sun, Aug 30
PHL
Philadelphia
MSN
Madison
$268 Roundtrip, found 4 days ago
$268
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Aug 27 from Philadelphia to Madison, returning Sun, Aug 30, priced at $268 found 4 days ago
Sat, Dec 12 - Wed, Dec 16
ABE
Allentown
RFD
Rockford
$278 Roundtrip, found 6 days ago
$278
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Dec 12 from Allentown to Rockford, returning Wed, Dec 16, priced at $278 found 6 days ago

Southern Wisconsin economy flight packages

Price found within the past 48 hours. Click for updated prices.
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! (2,507 reviews)

Jul 12 - Jul 16

4 night stay

Philadelphia (PHL) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,385, price is now $1,008 per person
$1,008
per person
found 1 day ago
Really nice property, rooms were clean, and staff was extremely friendly

Reviewed on May 5, 2026

The Langham, Chicago
5.0-star property

The Langham, Chicago

9.8/10 Exceptional! (1,006 reviews)

Jul 9 - Jul 12

3 night stay

Philadelphia (PHL) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,729, price is now $1,203 per person
$1,203
per person
found 1 day ago
Just an absolutely beautiful hotel with spectacular service. Highly recommend.

Reviewed on Mar 29, 2024

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,001 reviews)

Jul 9 - Jul 12

3 night stay

Philadelphia (PHL) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,851, price is now $1,322 per person
$1,322
per person
found 1 day 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

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More About Flying To Southern Wisconsin from Philadelphia

Route Information for Flights from Philadelphia to Southern Wisconsin

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

Philadelphia to Southern Wisconsin

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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.