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 $983, price is now $665 per person
$665
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,328, price is now $860 per person
$860
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,089, price is now $761 per person
$761
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the sauna and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,312, price is now $921 per person
$921
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $948, price is now $679 per person
$679
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Dry cleaning, luggage storage, and wedding services are also on offer.

Top West Side hotels deals

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
$214 nightly
The price is $255 total per night
$255 total
Oct 25 - Oct 26
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
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
$175 nightly
The price is $208 total per night
$208 total
Oct 25 - Oct 26
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
LIVN - West Loop Chicago

LIVN - West Loop Chicago

4 out of 5
555 West Jackson Boulevard Chicago IL
$244 nightly
The price is $286 total per night
$286 total
Oct 1 - Oct 2
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
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
$291 nightly
The price is $345 total per night
$345 total
Oct 4 - Oct 5
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
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
155 N. Peoria Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$493 nightly
The price is $586 total per night
$586 total
Oct 25 - Oct 26
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
The Hoxton, Chicago

The Hoxton, Chicago

4 out of 5
200 N Green Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$304 nightly
The price is $362 total per night
$362 total
Oct 4 - Oct 5
Total with taxes and fees
This smoke-free hotel features 2 restaurants, 3 bars/lounges, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Valet parking, a coffee shop, and dry cleaning are also offered.
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 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 $665. 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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