Search Deals onDowntown Chicago Vacation Packages
Downtown Chicago Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Oak Brook Suites
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this business-friendly hotel in Villa Park. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Drury Lane Theater and Oakbrook Center Mall are located nearby.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 15
found 22 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 4-star 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.
La Banque Hotel
Save 100% on your flight
per person
Jul 10 - Jul 15
found 22 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 15
found 22 hours ago
Roundtrip flight included
Dallas (DAL) 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.
Sofitel Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 15
found 23 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 4.5-star luxury 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 15
found 23 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 15
found 22 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Dorothy's
Lakeview
Save 100% on your flight
per person
Jul 10 - Jul 15
found 22 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 3-star B&B in Chicago. Enjoy free breakfast, free WiFi, and laundry facilities. Popular attractions Wrigley Field and Michigan Avenue 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
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 ...
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 ...
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
Fairmont Chicago at Millennium Park
200 North Columbus Drive, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Swissotel - Chicago
323 E Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
Hotel Felix River North/Magnificent Mile
111 W Huron St, Chicago, IL
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
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.
Mon, Jul 7 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$150 Roundtrip, just found
$150
Roundtrip
just found
Mon, Jul 14 - Tue, Jul 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$257 Roundtrip, just found
$257
Roundtrip
just found
Tue, Aug 26 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$583 Roundtrip, found 2 days ago
$583
Roundtrip
found 2 days ago
Thu, Jun 19 - Mon, Aug 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$966 Roundtrip, found 1 day ago
$966
Roundtrip
found 1 day ago
Discover Other Travel Deals
- Navy Pier Vacations
- Michigan Avenue Vacations
- Millennium Park Vacations
- Grant Park Vacations
- Chicago Riverwalk Vacations
- Art Institute of Chicago Vacations
- Willis Tower Vacations
- Chicago Theatre Vacations
- Merchandise Mart Vacations
- Water Tower Place Vacations
- Cloud Gate Vacations
- State Street Vacations