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Downtown Vacation Packages

Downtown Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG

Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG

2.5 out of 5
Price was $419, price is now $287 per person
$287
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Cabela's and NOW Arena are located nearby.
Hotel Versey Chicago Lincoln Park

Hotel Versey Chicago Lincoln Park

3 out of 5
Lakeview
Price was $631, price is now $331 per person
$331
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,151, price is now $457 per person
$457
per person
Dec 21 - Dec 25
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, breakfast (surcharge), and a 24-hour 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $2,337, price is now $1,291 per person
$1,291
per person
Dec 13 - Dec 20
found 20 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $919, price is now $524 per person
$524
per person
Dec 23 - Dec 28
found 21 hours 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $560, price is now $335 per person
$335
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip non-stop 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.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $523, price is now $344 per person
$344
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $526, price is now $347 per person
$347
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip non-stop 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.

3-4 Night Vacations in Downtown

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
Save 100% on your flight
Price was $298, price is now $204 per person
$204
per person
Dec 11 - Dec 14
found 11 hours 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 $1,151, price is now $457 per person
$457
per person
Dec 21 - Dec 25
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
Save 100% on your flight
Price was $490, price is now $244 per person
$244
per person
Dec 11 - Dec 14
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 $1,006, price is now $678 per person
$678
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

5-7 Night Vacations in Downtown

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was $618, price is now $315 per person
$315
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Versey Chicago Lincoln Park

Hotel Versey Chicago Lincoln Park

3 out of 5
Lakeview
Price was $631, price is now $331 per person
$331
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
DoubleTree by Hilton Chicago - North Shore Conference Center

DoubleTree by Hilton Chicago - North Shore Conference Center

4 out of 5
Price was $553, price is now $335 per person
$335
per person
Dec 2 - Dec 8
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
Price was $2,337, price is now $1,291 per person
$1,291
per person
Dec 13 - Dec 20
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) 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
Fri, Nov 14 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Nov 14 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 19, priced at $112 just found
Frontier Airlines
Wed, Nov 5 - Sat, Nov 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$188 Roundtrip, found 3 days ago
$188
Roundtrip
found 3 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 3 days ago
Bargain Flight
Sat, Nov 15 - Sun, Nov 16
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$280 Roundtrip, found 4 hours ago
$280
Roundtrip
found 4 hours 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 4 hours ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$389 Roundtrip, found 11 hours ago
$389
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Jan 9 from Los Angeles Intl. to Greater Rockford, returning Sun, Jan 11, priced at $389 found 11 hours ago