West Side Vacation Packages 2026 from $295

West Side flight + hotel vacation packages

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

theWit Chicago, a Hilton Hotel

Downtown Chicago

Save 100% on your flight

$295

per person

Mar 20 - Mar 23

found 13 hours ago

Roundtrip flight included

Austin (AUS) 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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$297

per person

Mar 9 - Mar 12

found 11 hours ago

Roundtrip flight included

Austin (AUS) 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

Downtown Chicago

Save 100% on your flight

$342

per person

Mar 20 - Mar 23

found 13 hours ago

Roundtrip flight included

Austin (AUS) 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 Emily Hotel

Downtown Chicago

Save 100% on your flight

$386

per person

Mar 20 - Mar 23

found 13 hours ago

Roundtrip flight included

Austin (AUS) 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.

4BR Corporate Suite Central and Modern

Near North Side

Save 100% on your flight

$1,448

per person

Mar 12 - Mar 16

found 6 hours ago

Roundtrip flight included

Austin (AUS) to Chicago (ORD)

A 24-hour gym, self parking, and a virtual front desk are featured at this apartment. WiFi in public areas is free.

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

$95 nightly

$111 total

Jan 11 - Jan 12

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

$107 nightly

$126 total

Jan 8 - Jan 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

Hyatt House Chicago Medical/University District

1835 West Harrison Street Chicago IL

$101 nightly

$119 total

Jan 14 - Jan 15

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

The Hoxton Chicago

200 N Green Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$172 nightly

$201 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

Hampton Inn & Suites Chicago Medical District UIC

710 S Seeley Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$115 total

Jan 15 - Jan 16

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

155 N. Peoria Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$310 nightly

$364 total

Jan 11 - Jan 12

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.

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 $295. 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.