West Side Vacation Packages 2025/2026 from $295

West Side flight + hotel vacation packages

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

Staybridge Suites, Lincolnshire by IHG

Half Day

Save 100% on your flight

$295

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free perks include buffet breakfast, free self parking, and an area shuttle.

La Banque Hotel

Save 100% on your flight

$561

per person

Nov 7 - Nov 12

found 14 hours ago

Roundtrip flight included

Los Angeles (LAX) 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.

Baymont by Wyndham Chicago/Alsip

Save 100% on your flight

$298

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (MDW)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$1,583

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Save 100% on your flight

$603

per person

Sep 24 - Sep 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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

Top West Side hotels deals

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street, Chicago, IL

Free Cancellation

$133 nightly

$156 total

Aug 24 - Aug 25

Total includes 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

$162 nightly

$190 total

Aug 24 - Aug 25

Total includes taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Self parking, a terrace, and a snack bar/deli are also offered.

Pool

Free WiFi

Hyatt Place Chicago Medical/University District

1835 W Harrison Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$162 nightly

$190 total

Sep 1 - Sep 2

Total includes 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 Emily Hotel

311 North Morgan Street, Chicago, IL

$225 nightly

$265 total

Aug 24 - Aug 25

Total includes 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

Hotel Chicago West Loop, SureStay Collection by Best Western

1622 W Jackson Blvd, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$152 total

Sep 1 - Sep 2

Total includes taxes and fees

A 24-hour gym, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. Business travelers can take advantage of the 24-hour business center.

Pet friendly

Free WiFi

The Hoxton Chicago

200 N Green Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$229 nightly

$269 total

Sep 1 - Sep 2

Total includes 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.

Popular places to visit

United Center

4.5/5(701 reviews)

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

4/5(832 reviews)

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

Humboldt Park

3.5/5(2 reviews)

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 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 $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.