Search Deals onDowntown Chicago Vacation Packages
Downtown Chicago Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was $1,245, price is now $837 per person
$837
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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
Downtown Chicago
Save 100% on your flight
Price was $1,503, price is now $965 per person
$965
per person
Aug 26 - Aug 30
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.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,635, price is now $1,079 per person
$1,079
per person
Aug 5 - Aug 11
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 United Center and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,460, price is now $969 per person
$969
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,641, price is now $1,104 per person
$1,104
per person
Aug 27 - Aug 31
found 15 hours 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.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,894, price is now $1,317 per person
$1,317
per person
Aug 5 - Aug 11
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 rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,254, price is now $872 per person
$872
per person
Aug 27 - Aug 31
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,720, price is now $1,953 per person
$1,953
per person
Aug 5 - Aug 11
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.
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
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
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 ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
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 ...
River Hotel
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
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.
Sat, Sep 5 - Tue, Sep 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$206 Roundtrip, found 7 hours ago
$206
Roundtrip
found 7 hours ago
Tue, Aug 18 - Sat, Sep 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$269 Roundtrip, found 1 day ago
$269
Roundtrip
found 1 day ago
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$425 Roundtrip, found 6 days ago
$425
Roundtrip
found 6 days ago
Wed, Jul 8 - Wed, Jul 22
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$823 Roundtrip, found 20 hours ago
$823
Roundtrip
found 20 hours ago
Discover Other Travel Deals
- Navy Pier Vacations
- Chicago Riverwalk Vacations
- Millennium Park Vacations
- Michigan Avenue Vacations
- Grant Park Vacations
- Willis Tower Vacations
- Art Institute of Chicago Vacations
- Chicago Theatre Vacations
- Cloud Gate Vacations
- Water Tower Place Vacations
- Merchandise Mart Vacations
- Oak Street Beach Vacations