Search Deals onDowntown Chicago Vacation Packages
Downtown Chicago Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Place Itasca
Save 100% on your flight
Price was $326, price is now $230 per person
$230
per person
Apr 25 - Apr 29
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Itasca. 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 Allstate Arena are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,349, price is now $791 per person
$791
per person
May 1 - May 5
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.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $850, price is now $560 per person
$560
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $985, price is now $661 per person
$661
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hilton Chicago O'Hare Airport
O'Hare
Price was $744, price is now $519 per person
$519
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $806, price is now $565 per person
$565
per person
Apr 15 - Apr 19
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $844, price is now $599 per person
$599
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $807, price is now $577 per person
$577
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park 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
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 ...
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
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 ...
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 ...
Eurostars Magnificent Mile
660 North State Street Chicago IL
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Hilton Chicago
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Aloft Chicago Mag Mile
243 E. Ontario Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
The Wade
644 N Lake Shore Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
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.
Wed, May 6 - Sat, May 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Wed, Apr 15 - Mon, Apr 20
LAX
Los Angeles Intl.
MDW
Midway Intl.
$231 Roundtrip, found 4 hours ago
$231
Roundtrip
found 4 hours ago
Tue, Mar 17 - Wed, Mar 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$408 Roundtrip, found 3 days ago
$408
Roundtrip
found 3 days ago
Sat, May 30 - Mon, Sep 7
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,047 Roundtrip, found 1 day ago
$1,047
Roundtrip
found 1 day ago
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