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Downtown Vacation Packages

Downtown Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $483, price is now $344 per person
$344
per person
Mar 21 - Mar 25
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 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 $924, price is now $556 per person
$556
per person
Mar 13 - Mar 17
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,293, price is now $845 per person
$845
per person
Mar 13 - Mar 17
found 1 day 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
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 $1,167, price is now $801 per person
$801
per person
Mar 13 - Mar 17
found 1 day 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 2 restaurants. 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 $939, price is now $663 per person
$663
per person
Mar 13 - Mar 17
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.
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 $688, price is now $487 per person
$487
per person
Mar 13 - Mar 17
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, 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.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Price was $529, price is now $377 per person
$377
per person
Mar 10 - Mar 15
found 17 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois Beach State Park and Carmel Park are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $683, price is now $489 per person
$489
per person
Mar 13 - Mar 17
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.

3-4 Night Vacations in Downtown

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $351, price is now $255 per person
$255
per person
Mar 6 - Mar 9
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 $864, price is now $549 per person
$549
per person
Mar 12 - Mar 15
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 $1,083, price is now $740 per person
$740
per person
Mar 12 - Mar 15
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 $939, price is now $663 per person
$663
per person
Mar 13 - Mar 17
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.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Price was $529, price is now $377 per person
$377
per person
Mar 10 - Mar 15
found 17 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $806, price is now $493 per person
$493
per person
Mar 5 - Mar 10
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,587, price is now $1,038 per person
$1,038
per person
Mar 11 - Mar 16
found 19 hours 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
Price was $708, price is now $502 per person
$502
per person
Mar 5 - Mar 10
found 18 hours ago
Roundtrip flight included
Dallas (DFW) 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 hotel in South Haven. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
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 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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Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy

2 out of 5
117 55th St Grand Junction MI
Stay at this cabin in Grand Junction. Enjoy free parking, patios, and climate control. Popular attractions Saddle Lake and Breedsville North Park are located ...
Opens in a new windowPostcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
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
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
Holiday Inn Express South Haven by IHG

Holiday Inn Express South Haven by IHG

2.5 out of 5
72095 CR 388 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 breakfast and the helpful ...
Opens in a new windowHoliday Inn Express South Haven by IHG
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
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, Feb 26 - Tue, Mar 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$141 Roundtrip, found 18 hours ago
$141
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Thu, Feb 26 from Los Angeles Intl. to O'Hare Intl., returning Tue, Mar 3, priced at $141 found 18 hours ago
Frontier Airlines
Thu, Apr 9 - Mon, Apr 13
LAX
Los Angeles Intl.
MDW
Midway Intl.
$190 Roundtrip, found 2 hours ago
$190
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Los Angeles Intl. to Midway Intl., returning Mon, Apr 13, priced at $190 found 2 hours ago
American Airlines
Tue, Mar 17 - Wed, Mar 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$242 Roundtrip, found 2 hours ago
$242
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Mar 17 from Los Angeles Intl. to Greater Rockford, returning Wed, Mar 25, priced at $242 found 2 hours ago
American Airlines
Thu, Feb 26 - Fri, Mar 6
LAX
Los Angeles Intl.
AZO
Kalamazoo-Battle Creek Intl.
$305 Roundtrip, found 3 days ago
$305
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Feb 26 from Los Angeles Intl. to Kalamazoo-Battle Creek Intl., returning Fri, Mar 6, priced at $305 found 3 days ago