Search Deals onDowntown Vacation Packages
Downtown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $747, price is now $449 per person
$449
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sand Hill On The Lake
Price was $769, price is now $556 per person
$556
per person
May 23 - May 27
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this hotel in Lake Geneva. Enjoy free WiFi, free parking, and a private beach. Popular attractions Geneva National Golf Club and Lake Como are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Price was $1,142, price is now $856 per person
$856
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel 55 Chicago Downtown
Downtown Chicago
Price was $687, price is now $523 per person
$523
per person
May 8 - May 13
found 1 day ago
Roundtrip non-stop 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.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,662, price is now $1,092 per person
$1,092
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,178, price is now $793 per person
$793
per person
May 22 - May 26
found 20 hours ago
Roundtrip non-stop 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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,396, price is now $945 per person
$945
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,043, price is now $741 per person
$741
per person
May 21 - May 25
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 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.
3-4 Night Vacations in Downtown
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Downtown
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Downtown
Old Harbor Inn
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 ...
Historic Hotel Nichols
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 South Haven Center ...
Starlite Resort
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. ...
Save an average of 15% on thousands of hotels when you're signed in
Baymont by Wyndham South Haven
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 ...
Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
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 ...
Holiday Inn Express South Haven by IHG
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 ...
AmericInn by Wyndham Douglas/Saugatuck
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 ...
Lake Bluff Inn and Suites
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 ...
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.
Wed, Apr 22 - Tue, May 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 1 hour ago
$83
Roundtrip
found 1 hour ago
Fri, Apr 17 - Tue, Apr 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$219 Roundtrip, found 3 hours ago
$219
Roundtrip
found 3 hours ago
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$416 Roundtrip, found 1 hour ago
$416
Roundtrip
found 1 hour ago
Mon, Apr 13 - Sat, May 2
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$1,079 Roundtrip, found 14 hours ago
$1,079
Roundtrip
found 14 hours ago
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