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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.
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
Price was $415, price is now $225 per person
$225
per person
Feb 21 - Feb 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $566, price is now $311 per person
$311
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $464, price is now $265 per person
$265
per person
Mar 23 - Mar 26
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.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flight
Price was $1,708, price is now $982 per person
$982
per person
Mar 12 - Mar 17
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $612, price is now $355 per person
$355
per person
Mar 23 - Mar 26
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 Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $591, price is now $351 per person
$351
per person
Mar 23 - Mar 26
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, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $641, price is now $382 per person
$382
per person
Mar 23 - Mar 26
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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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 $673, price is now $416 per person
$416
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 Route 66 Raceway and Harrah's Casino 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 $398, price is now $205 per person
$205
per person
Feb 21 - Feb 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $415, price is now $225 per person
$225
per person
Feb 21 - Feb 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $566, price is now $311 per person
$311
per person
Mar 23 - Mar 26
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 $612, price is now $355 per person
$355
per person
Mar 23 - Mar 26
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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $735, price is now $366 per person
$366
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $751, price is now $389 per person
$389
per person
Mar 3 - Mar 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 $931, price is now $502 per person
$502
per person
Mar 22 - Mar 27
found 8 hours 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
Price was $1,503, price is now $820 per person
$820
per person
Mar 3 - Mar 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
Sat, Jan 31 - Tue, Feb 3
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$70 Roundtrip, found 6 days ago
$70
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jan 31 from Orlando Intl. to General Mitchell Intl., returning Tue, Feb 3, priced at $70 found 6 days ago
Frontier Airlines
Wed, Feb 18 - Mon, Feb 23
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Feb 18 from Hartsfield-Jackson Atlanta Intl. to General Mitchell Intl., returning Mon, Feb 23, priced at $118 found 1 day ago
Frontier Airlines
Wed, Jan 21 - Sat, Jan 31
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Jan 21 from Dallas-Fort Worth Intl. to General Mitchell Intl., returning Sat, Jan 31, priced at $159 found 5 days ago
Frontier Airlines
Wed, Mar 25 - Tue, Mar 31
DEN
Denver Intl.
MKE
General Mitchell Intl.
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Mar 25 from Denver Intl. to General Mitchell Intl., returning Tue, Mar 31, priced at $160 found 2 days ago