Search Deals onDowntown Chicago Vacation Packages
Downtown Chicago Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Place Chicago/ Schaumburg
Save 100% on your flight
Price was $395, price is now $251 per person
$251
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Woodfield Mall and Jump Zone are located nearby.
Sand Hill On The Lake
Price was $1,305, price is now $855 per person
$855
per person
Dec 20 - Dec 28
found 14 hours ago
Roundtrip flight included
Dallas (DFW) 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.
The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,184, price is now $491 per person
$491
per person
Dec 27 - Dec 31
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.
Level Chicago – Old Town
Downtown Chicago
Price was $1,087, price is now $558 per person
$558
per person
Dec 24 - Dec 31
found 9 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.
DoubleTree by Hilton Chicago - North Shore Conference Center
Save 100% on your flight
Price was $662, price is now $389 per person
$389
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Skokie. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions North Shore Center for the Performing Arts and Skokie Theatre are located nearby.
DoubleTree by Hilton Chicago - Alsip
Save 100% on your flight
Price was $425, price is now $271 per person
$271
per person
Dec 18 - Dec 22
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
Stay at this 4-star business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hollywood Park and Gaelic Park are located nearby.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
Save 100% on your flight
Price was $603, price is now $384 per person
$384
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star eco-certified hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). 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
Downtown Chicago
Save 100% on your flight
Price was $930, price is now $598 per person
$598
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip 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.
3-4 Night Vacations in Downtown Chicago
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Downtown Chicago
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Downtown Chicago
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Save an average of 15% on thousands of hotels when you're signed in
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
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. ...
Aloft Chicago Mag Mile
243 E. Ontario, Chicago, IL
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the bar in our reviews. Popular ...
Freehand Chicago
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
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.
Fri, Nov 14 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 4 days ago
$112
Roundtrip
found 4 days ago
Tue, Dec 2 - Sat, Dec 6
LAX
Los Angeles Intl.
MDW
Midway Intl.
$150 Roundtrip, found 3 hours ago
$150
Roundtrip
found 3 hours ago
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$372 Roundtrip, found 14 hours ago
$372
Roundtrip
found 14 hours ago
Thu, Dec 4 - Mon, Dec 15
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$590 Roundtrip, found 19 hours ago
$590
Roundtrip
found 19 hours ago
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