South Side Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
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South Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $338, price is now $236 per person
$236
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $652, price is now $375 per person
$375
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $513, price is now $316 per person
$316
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $727, price is now $485 per person
$485
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $649, price is now $445 per person
$445
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $482, price is now $336 per person
$336
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Hotel Deals
Baymont by Wyndham South Haven
1555 Phoenix Rd, I-196 Exit 20, South Haven, MI
3.05 km from South Side
Book a stay at this business-friendly hotel in South Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Old Harbor Inn
515 Williams Street, South Haven, MI
1.32 km from South Side
Stay at this 3-star hotel in South Haven. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean ...
Captain's Quarters Motel
3242 Blue Star Highway, Saugatuck, MI
29.79 km from South Side
Stay at this motel in Saugatuck. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Lake Bluff Inn and Suites
76648 11th Avenue, South Haven, MI
1.92 km from South Side
Book a stay at this family-friendly hotel in South Haven. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Deerlick Creek Beach Park and ...
AmericInn by Wyndham Douglas/Saugatuck
2905 Blue Star Hwy, Douglas, MI
26.84 km from South Side
Book a stay at this business-friendly hotel in Douglas. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Starlite Resort
3353 Blue Star Highway, Saugatuck, MI
30.73 km from South Side
Stay at this motel in Saugatuck. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Holiday Inn Express South Haven by IHG
72095 CR 388, South Haven, MI
3.16 km from South Side
Book a stay at this business-friendly hotel in South Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Yelton Manor Bed & Breakfast
140 North Shore Drive, South Haven, MI
1.46 km from South Side
Stay at this 3-star B&B in South Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Michigan Maritime Museum and Warner Vineyards ...
Country Inn & Suites by Radisson, South Haven, MI
1741 Phoenix St, South Haven, MI
3.38 km from South Side
Book a stay at this business-friendly hotel in South Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
117 55th St, Grand Junction, MI
17.04 km from South Side
Stay at this cabin in Grand Junction. Enjoy free parking, patios, and climate control. Popular attractions Saddle Lake and Breedsville North Park are located ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Dec 22 - Wed, Dec 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 5 days ago
$172
Roundtrip
found 5 days ago
Fri, Dec 26 - Mon, Dec 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$404 Roundtrip, found 2 days ago
$404
Roundtrip
found 2 days ago
Fri, Dec 26 - Mon, Dec 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$772 Roundtrip, found 2 days ago
$772
Roundtrip
found 2 days ago
Sun, Aug 2 - Sun, Aug 16
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$883 Roundtrip, found 6 days ago
$883
Roundtrip
found 6 days ago
Sun, Aug 2 - Sun, Aug 16
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$937 Roundtrip, found 6 days ago
$937
Roundtrip
found 6 days ago