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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.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Save 100% on your flight
Price was $813, price is now $507 per person
$507
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and 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 $1,403, price is now $809 per person
$809
per person
Oct 1 - Oct 5
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.
Excelente hotel, desayuno y ubicación 😉

Reviewed on Jul 31, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,393, price is now $852 per person
$852
per person
Oct 1 - Oct 5
found 1 day 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. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Comes with all the comforts of Home.

Reviewed on Jul 29, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $886, price is now $565 per person
$565
per person
Oct 1 - Oct 5
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.
Great location

Reviewed on Jul 31, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,293, price is now $826 per person
$826
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,368, price is now $892 per person
$892
per person
Sep 25 - Sep 27
found 4 hours ago
Roundtrip 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 Riverside Theater 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 $1,119, price is now $753 per person
$753
per person
Sep 25 - Sep 29
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 - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,007, price is now $687 per person
$687
per person
Sep 11 - Sep 14
found 1 day 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.
This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities

Reviewed on Jul 30, 2026

Southeast Wisconsin Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $813, price is now $507 per person
$507
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,403, price is now $809 per person
$809
per person
Oct 1 - Oct 5
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 $1,393, price is now $852 per person
$852
per person
Oct 1 - Oct 5
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 $1,423, price is now $890 per person
$890
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Milwaukee (MKE)

Southeast Wisconsin Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $974, price is now $564 per person
$564
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,711, price is now $953 per person
$953
per person
Sep 23 - 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 $1,634, price is now $921 per person
$921
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was $4,634, price is now $2,689 per person
$2,689
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Tue, Sep 1 - Tue, Sep 8
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$161 Roundtrip, found 5 hours ago
$161
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Sep 1 from Orlando Intl. to General Mitchell Intl., returning Tue, Sep 8, priced at $161 found 5 hours ago
Sun Country Airlines
Wed, Nov 25 - Sun, Nov 29
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Wed, Nov 25 from Minneapolis - St. Paul Intl. to General Mitchell Intl., returning Sun, Nov 29, priced at $217 found 1 day ago
Bargain Flight
Sat, Aug 15 - Tue, Sep 1
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$227 Roundtrip, found 2 days ago
$227
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sat, Aug 15 from Philadelphia Intl. to General Mitchell Intl., returning Tue, Sep 1, priced at $227 found 2 days ago
Bargain Flight
Mon, Aug 10 - Thu, Aug 27
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$249 Roundtrip, found 2 days ago
$249
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Mon, Aug 10 from Dallas-Fort Worth Intl. to General Mitchell Intl., returning Thu, Aug 27, priced at $249 found 2 days ago