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 Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,024, price is now $631 per person
$631
per person
Nov 26 - Dec 1
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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,199, price is now $674 per person
$674
per person
Oct 29 - Nov 2
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,912, price is now $1,116 per person
$1,116
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,512, price is now $910 per person
$910
per person
Nov 28 - Dec 4
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, laundry facilities, and concierge services are also on offer.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,739, price is now $1,131 per person
$1,131
per person
Oct 28 - Nov 3
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.

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 acclaimed theater scene.
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 $631. 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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