Search Deals onDowntown Chicago Vacation Packages
Downtown Chicago Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Four Points by Sheraton Chicago Schaumburg
Save 100% on your flight
Price was $503, price is now $328 per person
$328
per person
Oct 8 - Oct 14
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Woodfield Mall and Spring Valley are located nearby.
La Banque Hotel
Save 100% on your flight
Price was $933, price is now $532 per person
$532
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Staybridge Suites, Lincolnshire by IHG
Half Day
Save 100% on your flight
Price was $572, price is now $334 per person
$334
per person
Oct 8 - Oct 14
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Lincolnshire. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Marriott Theatre and Valentino Vineyards are located nearby.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove
Price was $629, price is now $371 per person
$371
per person
Sep 25 - Sep 30
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star golf hotel in Downers Grove. Enjoy free parking, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Morton Arboretum and Yorktown Shopping Center are located nearby.
Baymont by Wyndham Chicago/Alsip
Save 100% on your flight
Price was $551, price is now $332 per person
$332
per person
Oct 8 - Oct 14
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
Book a stay at this business-friendly hotel in Alsip. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hollywood Park and Gaelic Park are located nearby.
Hilton Chicago/Oak Lawn
Save 100% on your flight
Price was $777, price is now $487 per person
$487
per person
Oct 8 - Oct 14
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Oak Lawn. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Ridge Shopping Mall and SeatGeek Stadium are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,322, price is now $849 per person
$849
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,642, price is now $1,078 per person
$1,078
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
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
The Wade
644 N Lake Shore Dr, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
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 ...
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. ...
Save an average of 15% on thousands of hotels when you're signed in
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
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. ...
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
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 ...
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. ...
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.
Sun, Sep 14 - Sat, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Thu, Sep 11 - Mon, Sep 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$187 Roundtrip, found 2 days ago
$187
Roundtrip
found 2 days ago
Sun, Aug 24 - Sun, Aug 31
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$690 Roundtrip, found 4 days ago
$690
Roundtrip
found 4 days ago
Mon, Sep 22 - Sat, Oct 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$849 Roundtrip, found 6 days ago
$849
Roundtrip
found 6 days ago
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