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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.
Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel

Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel

3 out of 5
O'Hare
per person
Feb 23 - Feb 28
found 3 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 breakfast and the restaurant in our reviews. Popular attractions Wolff's Flea Market and Allstate Arena are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 9 - Feb 15
found 1 hour ago
Roundtrip non-stop flight included
Seattle (SEA) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Millennium Park are located nearby.
The Drake

The Drake

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 14 - Feb 19
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
DoubleTree by Hilton Chicago - North Shore Conference Center

DoubleTree by Hilton Chicago - North Shore Conference Center

4 out of 5
per person
Feb 23 - Feb 28
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Skokie. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions North Shore Center for the Performing Arts and Adagio Teas are located nearby.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.
Chicago Marriott Oak Brook

Chicago Marriott Oak Brook

3.5 out of 5
per person
Feb 23 - Feb 28
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3.5-star golf hotel in Oak Brook. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Oakbrook Center Mall and Drury Lane Theater are located nearby.
21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 and the clean rooms in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.
SpringHill Suites Chicago O'Hare by Marriott

SpringHill Suites Chicago O'Hare by Marriott

3 out of 5
Norwood Park
per person
Feb 23 - Feb 28
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Rosemont Theatre and Rivers Casino are located nearby.

3-4 Night Vacations in Near West Side

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Near West Side

Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 14 - Feb 19
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Feb 9 - Feb 15
found 1 hour ago
Roundtrip non-stop flight included
Seattle (SEA) to Chicago (ORD)

Cheap Hotel Deals in Near West Side

Hotel Chicago West Loop

Hotel Chicago West Loop

2.5 out of 5
1622 W Jackson Blvd, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff ...
Hotel Chicago West Loop
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
155 N. Peoria Street, Chicago, IL
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Nobu Hotel Chicago
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 free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
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River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
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. ...
Embassy Suites by Hilton Chicago Downtown River North
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Stay at this 4-star 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 ...
Eurostars Magnificent Mile
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
Hyatt Regency Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Hilton Chicago
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
Mon, Mar 17 - Tue, Mar 18
LAX
Los Angeles Intl.
MDW
Midway Intl.
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Mar 17 from Los Angeles Intl. to Midway Intl., returning Tue, Mar 18, priced at $115 just found
Frontier Airlines
Sat, Feb 8 - Mon, Feb 10
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 23 hours ago
$120
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Feb 8 from Los Angeles Intl. to O'Hare Intl., returning Mon, Feb 10, priced at $120 found 23 hours ago
Scandinavian Airlines
Sat, Mar 22 - Mon, Mar 31
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$537 Roundtrip, found 1 day ago
$537
Roundtrip
found 1 day ago
Select Scandinavian Airlines flight, departing Sat, Mar 22 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Mon, Mar 31, priced at $537 found 1 day ago
American Airlines
Tue, Feb 25 - Sun, Mar 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$937 Roundtrip, found 1 day ago
$937
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 25 from Pudong Intl. to O'Hare Intl., returning Sun, Mar 2, priced at $937 found 1 day ago