Search Deals onNear West Side Vacation Packages
Near West Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago/Midway Airport
Bedford Park
Save 100% on your flight
per person
Jul 4 - Jul 9
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall are located nearby.
Hampton Inn Chicago/Naperville
Save 100% on your flight
per person
Jul 17 - Jul 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Graduate by Hilton Evanston
Downtown Evanston
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Stay at this 4-star hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Baha'i House of Worship and Aragon Ballroom are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Jul 26 - Aug 1
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Garden Inn Chicago North Shore/Evanston
Downtown Evanston
Save 100% on your flight
per person
Jul 19 - Jul 24
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Baha'i House of Worship and Aragon Ballroom are located nearby.
Sonesta Chicago O'Hare Airport Rosemont
O'Hare
Save 100% on your flight
per person
Jul 13 - Jul 19
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
3-4 Night Vacations in Near West Side
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Near West Side
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Near West Side
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 ...
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
The Emily Hotel
311 North Morgan Street, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 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
Cozy and Modern Stay in the Heart of C
1407 w 15th St Chicago, Chicago, IL
Stay at this 3-star apartment in Chicago. Enjoy free WiFi, in-room washers/dryers, and air conditioning. Popular attractions United Center and Grant Park are ...
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 ...
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 ...
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 ...
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.
Fri, Oct 17 - Mon, Oct 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 16 hours ago
$140
Roundtrip
found 16 hours ago
Tue, Jul 15 - Sat, Jul 26
LAX
Los Angeles Intl.
MDW
Midway Intl.
$255 Roundtrip, found 1 day ago
$255
Roundtrip
found 1 day ago
Wed, Aug 27 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$555 Roundtrip, found 5 days ago
$555
Roundtrip
found 5 days ago
Thu, Jun 19 - Mon, Aug 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$966 Roundtrip, found 1 hour ago
$966
Roundtrip
found 1 hour ago