West Side Vacation Packages 2026 from $439

West Side flight + hotel vacation packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$439

per person

Jun 14 - Jun 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$491

per person

Jun 14 - Jun 17

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.

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$618

per person

Jun 19 - Jun 22

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 luxury hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$589

per person

Jun 14 - Jun 17

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. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$791

per person

Jun 14 - Jun 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

Top West Side hotels deals

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street Chicago IL

Free Cancellation

$135 nightly

$158 total

Apr 26 - Apr 27

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

Free Cancellation

Reserve now, pay when you stay

$227 nightly

$266 total

Apr 12 - Apr 13

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.

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street Chicago IL

Free Cancellation

$128 nightly

$151 total

Apr 12 - Apr 13

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.

Hyatt House Chicago West Loop

105 N MAY STREET Chicago IL

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$189 total

Apr 12 - Apr 13

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

The Hoxton Chicago

200 N Green Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$194 nightly

$228 total

Apr 12 - Apr 13

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.

Nobu Hotel Chicago

155 N. Peoria Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$339 nightly

$398 total

Apr 19 - Apr 20

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.

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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 fascinating museums.

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 theater scene and entertainment choices 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 $439. 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.