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Near West Side Vacation Packages

Near West Side Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,348, price is now $910 per person
$910
per person
Oct 14 - Oct 18
found 1 day 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,522, price is now $911 per person
$911
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,806, price is now $1,132 per person
$1,132
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,578, price is now $1,059 per person
$1,059
per person
Oct 23 - Oct 27
found 4 hours ago
Roundtrip flight included
Albuquerque (ABQ) 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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,722, price is now $1,176 per person
$1,176
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,504, price is now $1,063 per person
$1,063
per person
Oct 23 - Oct 27
found 4 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this luxury 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.
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
Save 100% on your flight
Price was $1,432, price is now $1,024 per person
$1,024
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and room service. Our guests praise the clean rooms in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Stay One Chicago

Stay One Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,499, price is now $1,084 per person
$1,084
per person
Oct 21 - Oct 25
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, private pools, and 3 restaurants. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

3-4 Night Vacations in Near West Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,029, price is now $724 per person
$724
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,578, price is now $1,059 per person
$1,059
per person
Oct 23 - Oct 27
found 4 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,148, price is now $796 per person
$796
per person
Oct 22 - Oct 25
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,504, price is now $1,063 per person
$1,063
per person
Oct 23 - Oct 27
found 4 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)

5-7 Night Vacations in Near West Side

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,522, price is now $911 per person
$911
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $2,144, price is now $1,375 per person
$1,375
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,023, price is now $1,160 per person
$1,160
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,806, price is now $1,132 per person
$1,132
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Cheap Hotel Deals in Near West Side

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Opens in a new windowCrowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
Opens in a new windowHoliday Inn & Suites Chicago - Downtown by IHG
Chicago Parthenon Hostel

Chicago Parthenon Hostel

2 out of 5
310 S. Halsted Street Chicago IL
Stay at this hostel in Chicago. Enjoy free WiFi, concierge services, and rainfall showerheads. Our guests praise the helpful staff in our reviews. Popular attractions ...
Opens in a new windowChicago Parthenon Hostel
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Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
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 ...
Opens in a new windowCongress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Opens in a new windowKasa Magnificent Mile Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Opens in a new windowRiver Hotel
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
Opens in a new windowHampton Inn Chicago Downtown/Magnificent Mile
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.

Frontier Airlines
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $138 just found
American Airlines
Fri, Nov 6 - Mon, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select American Airlines flight, departing Fri, Nov 6 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $217 just found
Southwest Airlines
Sat, Sep 26 - Sat, Oct 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$261 Roundtrip, just found
$261
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Sep 26 from Los Angeles Intl. to Midway Intl., returning Sat, Oct 3, priced at $261 just found
Asiana Airlines
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,066 Roundtrip, found 3 hours ago
$1,066
Roundtrip
found 3 hours ago
Select Asiana Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Mon, Nov 30, priced at $1,066 found 3 hours ago