Deals on vacations and trips to West Side

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West Side flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $967, price is now $678 per person
$678
per person
Oct 22 - Oct 24
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,573, price is now $986 per person
$986
per person
Oct 29 - Nov 3
found 18 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,261, price is now $837 per person
$837
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,649, price is now $1,123 per person
$1,123
per person
Oct 29 - Nov 3
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,182, price is now $810 per person
$810
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Top West Side hotels deals

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
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $185 total per night
$185 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.
Pet friendly
Free WiFi
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Free Cancellation
$154 nightly
The price is $183 total per night
$183 total
Sep 8 - Sep 9
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a snack bar/deli are also offered.
Pool
Free WiFi
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$275 nightly
The price is $327 total per night
$327 total
Aug 23 - Aug 24
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Pet friendly
Free WiFi
Hotel Chicago West Loop, SureStay Collection by Best Western

Hotel Chicago West Loop, SureStay Collection by Best Western

2.5 out of 5
1622 W Jackson Blvd Chicago IL
Free Cancellation
Reserve now, pay when you stay
$155 nightly
The price is $184 total per night
$184 total
Aug 11 - Aug 12
Total with taxes and fees
A 24-hour gym is featured at this hotel, along with free WiFi in public areas and express check-in. Business travelers can take advantage of the 24-hour business center. Express check-out, a computer station, and luggage storage are also on offer.
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
155 N. Peoria Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$440 nightly
The price is $523 total per night
$523 total
Aug 16 - Aug 17
Total with taxes and fees
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Pet friendly
LIVN - West Loop Chicago

LIVN - West Loop Chicago

4 out of 5
555 West Jackson Boulevard Chicago IL
$209 nightly
The price is $245 total per night
$245 total
Aug 16 - Aug 17
Total with taxes and fees
A 24-hour gym is featured at this hotel, along with free WiFi in public areas and luggage storage. Locker space, laundry facilities, and a virtual front desk are also on offer.
Free WiFi
Air conditioning
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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.

Stay near popular West Side attractions

A large, modern building with a curved facade and multiple vertical windows.

United Center

8.8/10 (4,269 reviews)
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
See properties

Frequently asked questions

How much are vacation packages to West Side?
Exciting adventures await in West Side, with Travelocity vacation packages starting from just $678. In addition to flights and hotels, these amazing deals make it easy to experience all corners of the world.
Where can I get the best vacation package deals for West Side?
Travelocity is the only place you need to go to score a great West Side package deal. Choose from as many as 400 air carriers and 1,000,000 properties across the globe and create a vacation package that suits your style. With this amount of choice at your fingertips, now's the time to book your next great adventure.
Why should I book my West Side vacation bundle with Travelocity?
You'll not only enjoy huge savings, but you'll also have access to our round-the-clock support, top-notch service and a Price Match Guarantee. Journey across the globe, discover hidden sights and forge lifelong memories — we'll take care of the important details.
Can I save on my West Side car rental if I book it with my hotel or flight?
Combining your bookings into a West Side vacation package will save you a tidy sum. Combine a flight and car; a flight, car and hotel; or a hotel and car. There's no better way to discover the greater West Side area than from the comfort of your own rental car. You can also add tours and experiences to your Travelocity package.
Which airport is best for West Side?
Most jet-setters head to West Side through O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW). Lewis University Airport (LOT) is another popular choice.
What is there to do in West Side?
West Side boasts hidden gems around every turn, but make sure you plan a trip to University of Illinois Chicago and United Center while you're in town. These attractions can't be missed.

Photos of local treasures

Browse West Side vacation photos for more inspiration

A greenhouse with a glass ceiling, various cacti, and a wooden structure in the center.
A city skyline at dusk with a prominent skyscraper and a body of water in the foreground.
A city street with a train passing overhead, cars, pedestrians, and a red brick building.
A busy city street with tall buildings, a bus, and cars.
A greenhouse with various plants and trees, a pathway, and a white door.

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