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Downtown Vacation Packages

3-4 Night Vacations in Downtown

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Save 100% on your flight
Price was $297, price is now $181 per person
$181
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $715, price is now $399 per person
$399
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 $373, price is now $237 per person
$237
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
Save 100% on your flight
Price was $594, price is now $385 per person
$385
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Downtown

Price found within the past 48 hours. Click for updated prices.
Hyatt Centric Chicago Ohare

Hyatt Centric Chicago Ohare

3.5 out of 5
Price was $554, price is now $366 per person
$366
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was $556, price is now $379 per person
$379
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop 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 $2,166, price is now $1,309 per person
$1,309
per person
Dec 22 - Dec 28
found 13 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,111, price is now $690 per person
$690
per person
Dec 22 - Dec 28
found 13 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)

Cheap Hotel Deals in Downtown

Old Harbor Inn

Old Harbor Inn

3 out of 5
515 Williams Street, South Haven, MI
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 ...
Opens in a new windowOld Harbor Inn
Historic Hotel Nichols

Historic Hotel Nichols

2 out of 5
201 Center St, South Haven, MI
Stay at this hotel in South Haven. Enjoy free WiFi, a conference center, and concierge services. Popular attractions Warner Vineyards and Michigan Maritime Museum ...
Opens in a new windowHistoric Hotel Nichols
Baymont by Wyndham South Haven

Baymont by Wyndham South Haven

2.5 out of 5
1555 Phoenix Rd, I-196 Exit 20, South Haven, MI
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 ...
Opens in a new windowBaymont by Wyndham South Haven
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Captain's Quarters Motel

Captain's Quarters Motel

2 out of 5
3242 Blue Star Highway, Saugatuck, MI
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 ...
Opens in a new windowCaptain's Quarters Motel
Lake Bluff Inn and Suites

Lake Bluff Inn and Suites

2.5 out of 5
76648 11th Avenue, South Haven, MI
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 ...
Opens in a new windowLake Bluff Inn and Suites
Best Western Plaza Hotel Saugatuck

Best Western Plaza Hotel Saugatuck

2.5 out of 5
3457 Blue Star Highway, Saugatuck, MI
Stay at this hotel in Saugatuck. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowBest Western Plaza Hotel Saugatuck
AmericInn by Wyndham Douglas/Saugatuck

AmericInn by Wyndham Douglas/Saugatuck

2 out of 5
2905 Blue Star Hwy, Douglas, MI
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 ...
Opens in a new windowAmericInn by Wyndham Douglas/Saugatuck
Starlite Resort

Starlite Resort

2.5 out of 5
3353 Blue Star Highway, Saugatuck, MI
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. ...
Opens in a new windowStarlite Resort
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

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

Spirit Airlines
Thu, Nov 27 - Tue, Dec 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Nov 27 from Los Angeles Intl. to O'Hare Intl., returning Tue, Dec 2, priced at $102 found 1 day ago
Frontier Airlines
Wed, Nov 5 - Sat, Nov 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$188 Roundtrip, found 5 days ago
$188
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Nov 5 from Los Angeles Intl. to Midway Intl., returning Sat, Nov 15, priced at $188 found 5 days ago
Bargain Flight
Sat, Nov 15 - Sun, Nov 16
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Sat, Nov 15 from Los Angeles Intl. to South Bend Intl., returning Sun, Nov 16, priced at $280 found 2 days ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$389 Roundtrip, found 2 days ago
$389
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Jan 9 from Los Angeles Intl. to Greater Rockford, returning Sun, Jan 11, priced at $389 found 2 days ago