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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $509, price is now $275 per person
$275
per person
May 8 - May 10
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.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
Price was $666, price is now $401 per person
$401
per person
May 1 - May 3
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Delafield Hotel

The Delafield Hotel

4 out of 5
Save 100% on your flight
Price was $1,464, price is now $889 per person
$889
per person
May 2 - May 9
found 5 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Delafield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Hawks Inn and Lapham Peak are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $906, price is now $562 per person
$562
per person
May 22 - May 25
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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,466, price is now $912 per person
$912
per person
May 1 - May 8
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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $597, price is now $376 per person
$376
per person
May 1 - May 4
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $796, price is now $501 per person
$501
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $686, price is now $435 per person
$435
per person
May 22 - May 25
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.

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 $653, price is now $312 per person
$312
per person
May 10 - May 13
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 $906, price is now $562 per person
$562
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $597, price is now $376 per person
$376
per person
May 1 - May 4
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $796, price is now $501 per person
$501
per person
May 22 - May 25
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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,245, price is now $701 per person
$701
per person
May 1 - May 8
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
Price was $2,198, price is now $846 per person
$846
per person
May 1 - May 8
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 $1,883, price is now $1,065 per person
$1,065
per person
May 1 - May 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,007, price is now $1,189 per person
$1,189
per person
May 1 - May 8
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
Mon, Mar 9 - Mon, Mar 23
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Mar 9 from Hartsfield-Jackson Atlanta Intl. to General Mitchell Intl., returning Mon, Mar 23, priced at $120 found 2 days ago
Frontier Airlines
Fri, Apr 10 - Mon, Apr 13
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$160 Roundtrip, found 10 hours ago
$160
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Fri, Apr 10 from Dallas-Fort Worth Intl. to General Mitchell Intl., returning Mon, Apr 13, priced at $160 found 10 hours ago
Frontier Airlines
Wed, Mar 25 - Tue, Mar 31
DEN
Denver Intl.
MKE
General Mitchell Intl.
$160 Roundtrip, found 11 hours ago
$160
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Wed, Mar 25 from Denver Intl. to General Mitchell Intl., returning Tue, Mar 31, priced at $160 found 11 hours ago
Frontier Airlines
Thu, Mar 19 - Sun, Apr 5
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$162 Roundtrip, found 14 hours ago
$162
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Thu, Mar 19 from Orlando Intl. to General Mitchell Intl., returning Sun, Apr 5, priced at $162 found 14 hours ago