Search Deals onDowntown Chicago Vacation Packages
Downtown Chicago Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Chicago-Carol Stream
Save 100% on your flight
per person
Jul 12 - Jul 19
found 14 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this hotel in Carol Stream. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Xtreme Trampolines and Cosley Zoo are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Austin (AUS) 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.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
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 the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
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. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Save 100% on your flight
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Chicago River Side Suites
Downtown Chicago
Save 100% on your flight
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, daily housekeeping, and slippers. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hampton Inn Chicago/Naperville
Save 100% on your flight
per person
Jul 12 - Jul 19
found 14 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Nike Sports Complex are located nearby.
Nobu Hotel Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chicago Riverwalk and United Center 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.
Tue, Jul 22 - Tue, Jul 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 20 hours ago
$140
Roundtrip
found 20 hours ago
Tue, Jul 15 - Sat, Jul 26
LAX
Los Angeles Intl.
MDW
Midway Intl.
$255 Roundtrip, found 2 days ago
$255
Roundtrip
found 2 days ago
Tue, Aug 26 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$583 Roundtrip, found 8 hours ago
$583
Roundtrip
found 8 hours 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
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