$71 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, Feb 14 - Mon, Feb 16
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$397 Roundtrip, found 2 days ago
$397
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Feb 14 from Philadelphia Intl. to General Mitchell Intl., returning Mon, Feb 16, priced at $397 found 2 days ago
Sun, Feb 15 - Wed, Feb 18
TTN
Mercer
MKE
General Mitchell Intl.
$443 Roundtrip, found 6 days ago
$443
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Feb 15 from Mercer to General Mitchell Intl., returning Wed, Feb 18, priced at $443 found 6 days ago
Sat, Feb 14 - Tue, Feb 17
PHL
Philadelphia Intl.
MSN
Dane County Regional
$475 Roundtrip, found 1 day ago
$475
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Feb 14 from Philadelphia Intl. to Dane County Regional, returning Tue, Feb 17, priced at $475 found 1 day ago
Fri, Feb 13 - Mon, Feb 16
PHL
Philadelphia Intl.
RFD
Greater Rockford
$689 Roundtrip, found 16 hours ago
$689
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Fri, Feb 13 from Philadelphia Intl. to Greater Rockford, returning Mon, Feb 16, priced at $689 found 16 hours ago

Airfares from $71 One Way, $152 Round Trip from Philadelphia to Southern Wisconsin

Prices starting at $152 for return flights and $71 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.

Thu, Feb 26 - Sat, Feb 28
TTN
Trenton
MKE
Milwaukee
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Trenton to Milwaukee, returning Sat, Feb 28, priced at $152 found 2 days ago
Tue, Feb 24 - Fri, Feb 27
PHL
Philadelphia
MKE
Milwaukee
$183 Roundtrip, found 1 hour ago
$183
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Feb 24 from Philadelphia to Milwaukee, returning Fri, Feb 27, priced at $183 found 1 hour ago
Wed, Mar 25 - Thu, Apr 9
PHL
Philadelphia
MSN
Madison
$195 Roundtrip, found 3 days ago
$195
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Mar 25 from Philadelphia to Madison, returning Thu, Apr 9, priced at $195 found 3 days ago
Wed, Feb 25 - Sat, Feb 28
PHL
Philadelphia
RFD
Rockford
$223 Roundtrip, found 6 days ago
$223
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Feb 25 from Philadelphia to Rockford, returning Sat, Feb 28, priced at $223 found 6 days ago
Wed, Mar 4 - Tue, Mar 10
ABE
Allentown
ATW
Appleton
$275 Roundtrip, found 2 days ago
$275
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Mar 4 from Allentown to Appleton, returning Tue, Mar 10, priced at $275 found 2 days ago

Southern Wisconsin economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
4.0-star property

The Emily Hotel

9.2/10 Wonderful! (1,264 reviews)

Apr 2 - Apr 8

6 night stay

Philadelphia (PHL) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Philadelphia (PHL)

Spirit Airlines • Coach
Save 100% on your flight
Price was $1,180, price is now $821 per person
$821
per person
found 22 hours ago
Cute and trendy hotwl but there was a loud party on-site which ruined experience. It felt clean but our mini fridge had takeout left from former guest, so maid service obviously missed that.

Reviewed on Jul 26, 2025

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (380 reviews)

Mar 9 - Mar 16

7 night stay

Philadelphia (PHL) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,565, price is now $1,114 per person
$1,114
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.

Reviewed on Nov 20, 2025

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,000 reviews)

Mar 29 - Apr 1

3 night stay

Philadelphia (PHL) to Chicago (ORD)

Frontier Airlines • Coach

Chicago (ORD) to Philadelphia (PHL)

Spirit Airlines • Coach
Price was $1,132, price is now $858 per person
$858
per person
found 21 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

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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.