West Side Vacation Packages 2026 from $368

West Side flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$368

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

Save 100% on your flight

$487

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

theWit Chicago, a Hilton Hotel

Downtown Chicago

Save 100% on your flight

$382

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.

La Banque Hotel

Save 100% on your flight

$539

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$418

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. 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.

Top West Side hotels deals

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$91 nightly

$107 total

Jan 25 - Jan 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

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street Chicago IL

Free Cancellation

$110 nightly

$129 total

Jan 17 - Jan 18

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

Hyatt House Chicago Medical/University District

1835 West Harrison Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$119 total

Jan 19 - Jan 20

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Breakfast included

Free WiFi

Hampton Inn & Suites Chicago Medical District UIC

710 S Seeley Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$128 total

Jan 18 - Jan 19

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

The Hoxton Chicago

200 N Green Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$174 nightly

$204 total

Jan 18 - Jan 19

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

Hyatt House Chicago West Loop

105 N MAY STREET Chicago IL

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$169 total

Jan 19 - Jan 20

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and free buffet breakfast each morning.

Pool

Breakfast included

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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.

Popular places to visit

United Center

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

University of Illinois Chicago

Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.

Humboldt Park

Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the fascinating museums and acclaimed art scene in this vibrant area.

Frequently asked questions

How much are vacation packages to West Side?

Exciting adventures await in West Side, with Travelocity vacation packages starting from just $368. 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.