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Southeast Wisconsin Vacation Packages

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Southeast Wisconsin Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $672, price is now $458 per person
$458
per person
Sep 24 - Sep 28
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicagoland Speedway and Route 66 Raceway are located nearby.
It was a wonderful experience.

Reviewed on Jul 16, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,450, price is now $862 per person
$862
per person
Sep 23 - Sep 28
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,201, price is now $753 per person
$753
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,148, price is now $753 per person
$753
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,020, price is now $681 per person
$681
per person
Oct 3 - Oct 6
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on Jul 14, 2026

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

2 out of 5
Save 100% on your flight
Price was $3,276, price is now $2,212 per person
$2,212
per person
Sep 15 - Sep 20
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,249, price is now $1,531 per person
$1,531
per person
Sep 1 - Sep 7
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions American Family Field and Fiserv Forum are located nearby.
We were in Milwaukee for our son’s engagement. I had scheduled some special deserts to be shipped from NewJersey. I had called the hotel and advised them to refrigerate the box immediately when received. I was assured that they would take care of it. However when we arrived, and were ready to leave for the engagement we were informed that they had put the box in the freezer instead of the refrigerator. Also the management did not make any attempt to apologize for messing this up for us. Extremely bad customer service.

Reviewed on Jul 14, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $834, price is now $573 per person
$573
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Awful experience will not be going back ever again

Reviewed on Jul 16, 2026

Southeast Wisconsin Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,201, price is now $753 per person
$753
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $1,455, price is now $898 per person
$898
per person
Sep 5 - Sep 8
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $1,385, price is now $883 per person
$883
per person
Oct 8 - Oct 11
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,148, price is now $753 per person
$753
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Southeast Wisconsin Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $1,237, price is now $707 per person
$707
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,002, price is now $1,132 per person
$1,132
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,643, price is now $932 per person
$932
per person
Sep 23 - Sep 28
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,094, price is now $1,220 per person
$1,220
per person
Sep 15 - Sep 20
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Mon, Oct 5 - Sat, Oct 17
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Oct 5 from Orlando Intl. to General Mitchell Intl., returning Sat, Oct 17, priced at $198 found 1 day ago
Bargain Flight
Fri, Aug 14 - Sun, Aug 16
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$215 Roundtrip, found 3 days ago
$215
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Fri, Aug 14 from Minneapolis - St. Paul Intl. to General Mitchell Intl., returning Sun, Aug 16, priced at $215 found 3 days ago
Bargain Flight
Sat, Oct 17 - Wed, Oct 21
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$235 Roundtrip, found 2 days ago
$235
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sat, Oct 17 from Philadelphia Intl. to General Mitchell Intl., returning Wed, Oct 21, priced at $235 found 2 days ago
Bargain Flight
Mon, Aug 10 - Thu, Aug 27
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$235 Roundtrip, found 13 hours ago
$235
Roundtrip
found 13 hours ago
Select Bargain Flight flight, departing Mon, Aug 10 from Dallas-Fort Worth Intl. to General Mitchell Intl., returning Thu, Aug 27, priced at $235 found 13 hours ago