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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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $355, price is now $186 per person
$186
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $634, price is now $329 per person
$329
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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 Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $705, price is now $370 per person
$370
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $777, price is now $432 per person
$432
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $426, price is now $238 per person
$238
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Price was $1,079, price is now $605 per person
$605
per person
Jan 22 - Jan 26
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). 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 $344, price is now $196 per person
$196
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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 $423, price is now $241 per person
$241
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.

Southeast Wisconsin Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $355, price is now $186 per person
$186
per person
Jan 16 - Jan 19
found 1 day 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 $634, price is now $329 per person
$329
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $777, price is now $432 per person
$432
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $426, price is now $238 per person
$238
per person
Jan 16 - Jan 19
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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was $712, price is now $303 per person
$303
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,621, price is now $605 per person
$605
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $894, price is now $400 per person
$400
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $862, price is now $415 per person
$415
per person
Jan 16 - Jan 23
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
Sat, Dec 20 - Tue, Dec 30
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$105 Roundtrip, found 13 hours ago
$105
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, Dec 20 from Orlando Intl. to General Mitchell Intl., returning Tue, Dec 30, priced at $105 found 13 hours ago
United
Sat, Jan 10 - Mon, Jan 12
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jan 10 from Dallas-Fort Worth Intl. to General Mitchell Intl., returning Mon, Jan 12, priced at $158 found 1 day ago
Delta
Sat, Dec 13 - Sat, Dec 13
SEA
Seattle - Tacoma Intl.
MKE
General Mitchell Intl.
$176 Roundtrip, found 2 days ago
$176
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Dec 13 from Seattle - Tacoma Intl. to General Mitchell Intl., returning Sat, Dec 13, priced at $176 found 2 days ago
American Airlines
Tue, Dec 9 - Wed, Dec 17
TPA
Tampa Intl.
MKE
General Mitchell Intl.
$177 Roundtrip, found 15 hours ago
$177
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Tue, Dec 9 from Tampa Intl. to General Mitchell Intl., returning Wed, Dec 17, priced at $177 found 15 hours ago