West Side Vacation Packages 2025/2026 from $273

West Side flight + hotel vacation packages

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

Hyatt House Chicago West Loop

Downtown Chicago

Save 100% on your flight

$273

per person

Feb 4 - Feb 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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

The Westin Michigan Avenue Chicago

Downtown Chicago

$516

per person

Dec 22 - Dec 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

Save 100% on your flight

$431

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. There's luggage storage and multilingual staff can provide around-the-clock assistance.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$918

per person

Dec 28 - Jan 2

found 6 hours ago

Roundtrip flight included

Atlanta (ATL) 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.

Holiday Inn Express Chicago - Magnificent Mile by IHG

Downtown Chicago

Save 100% on your flight

$308

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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

Top West Side hotels deals

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street Chicago IL

Free Cancellation

$95 nightly

$112 total

Dec 14 - Dec 15

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

Hyatt House Chicago Medical/University District

1835 West Harrison Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$151 total

Dec 7 - Dec 8

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 Emily Hotel

311 North Morgan Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$195 nightly

$229 total

Dec 7 - Dec 8

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

Hampton Inn & Suites Chicago Medical District UIC

710 S Seeley Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$102 total

Dec 7 - Dec 8

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

$327 nightly

$384 total

Nov 23 - Nov 24

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

Hyatt House Chicago West Loop

105 N MAY STREET Chicago IL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$198 total

Nov 23 - Nov 24

Total with taxes and fees

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 acclaimed theater scene.

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 art 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 $273. 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.