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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $985, price is now $608 per person
$608
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,541, price is now $878 per person
$878
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,649, price is now $942 per person
$942
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,039, price is now $666 per person
$666
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a snack bar/deli are also offered.
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 $1,065, price is now $702 per person
$702
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

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
$184 nightly
The price is $219 total per night
$219 total
Aug 20 - Aug 21
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
$157 nightly
The price is $187 total per night
$187 total
Aug 9 - Aug 10
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
$275 nightly
The price is $327 total per night
$327 total
Aug 9 - Aug 10
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
$166 nightly
The price is $198 total per night
$198 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 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.
Pet friendly
Free WiFi
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
710 S Seeley Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$167 nightly
The price is $199 total per night
$199 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free full breakfast each morning.
Pool
Breakfast included
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
155 N. Peoria Street Chicago IL
$475 nightly
The price is $565 total per night
$565 total
Jul 26 - Jul 27
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
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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 $608. 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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