West Side Vacation Packages 2026 from $481

West Side flight + hotel vacation packages

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

Hilton Chicago O'Hare Airport

O'Hare

Save 100% on your flight

$481

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$554

per person

Aug 12 - Aug 15

found 22 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$1,111

per person

Jul 22 - Jul 26

found 5 hours ago

Roundtrip flight included

Dallas (DFW) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$957

per person

Aug 14 - Aug 17

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.

The Neighborhood Hotel-New Buffalo

Downtown New Buffalo

Save 100% on your flight

$805

per person

Jul 28 - Aug 1

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A communal living room, a picnic area, and express check-in are also on offer.

Top West Side hotels deals

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street Chicago IL

$145 nightly

$172 total

Jul 6 - Jul 7

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

The Emily Hotel

311 North Morgan Street Chicago IL

$289 nightly

$343 total

Jun 28 - Jun 29

Total with taxes and fees

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.

Pet friendly

Free WiFi

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$184 total

Jul 7 - Jul 8

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

Hampton Inn Chicago West Loop Fulton Market Area

116 North Jefferson Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$195 nightly

$232 total

Jul 1 - Jul 2

Total with taxes and fees

This hotel features a 24-hour gym and a rooftop terrace. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy the free buffet breakfast each morning.

Breakfast included

Pet friendly

Hotel Chicago West Loop, SureStay Collection by Best Western

1622 W Jackson Blvd Chicago IL

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$151 total

Jun 28 - Jun 29

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

Nobu Hotel Chicago

155 N. Peoria Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$356 nightly

$423 total

Jun 28 - Jun 29

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

Aerial view of the iconic John Hancock Center and shimmering skyscrapers meeting the tranquil blue of Lake Michigan's shoreline, Chicago, Illinois, United States.

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 acclaimed theater scene 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 acclaimed art scene and fascinating museums 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 $481. 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.