Search Deals onDowntown Chicago Vacation Packages
Downtown Chicago Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Residence Inn By Marriott Merrillville
Save 100% on your flight
per person
Sep 20 - Sep 24
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Merrillville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Westfield Southlake Mall and Turkey Creek Golf Course are located nearby.
The Stella Hotel & Ballroom
Downtown Kenosha
Save 100% on your flight
per person
Sep 20 - Sep 24
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (CHI)
Stay at this 3.5-star business-friendly hotel in Kenosha. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dinosaur Discovery Museum and Alpaca Art are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
DayDreamer Domes
Save 100% on your flight
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this 4-star hotel in South Haven. Enjoy free parking, room service, and onsite spa services. Popular attractions Kal Haven Trail and Michigan Maritime Museum are located nearby.
Baymont by Wyndham Chicago/Alsip
Save 100% on your flight
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Wyndham Garden Kenosha Harborside
Downtown Kenosha
Save 100% on your flight
per person
Sep 20 - Sep 24
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (CHI)
Stay at this 3.5-star business-friendly hotel in Kenosha. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kenosha History Center and Elsie Mae's Canning are located nearby.
La Banque Hotel
per person
Sep 1 - Sep 5
found 19 hours ago
Roundtrip flight included
Tulsa (TUL) 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.
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 ...
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
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. ...
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 Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
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 ...
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, Aug 16 - Tue, Aug 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Sat, Oct 25 - Sat, Oct 25
LAX
Los Angeles Intl.
MDW
Midway Intl.
$211 Roundtrip, found 1 day ago
$211
Roundtrip
found 1 day ago
Wed, Aug 27 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$620 Roundtrip, found 5 days ago
$620
Roundtrip
found 5 days ago
Mon, Sep 22 - Sat, Oct 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$849 Roundtrip, found 4 days ago
$849
Roundtrip
found 4 days ago
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