West Side Vacation Packages 2025/2026 from $243

West Side flight + hotel vacation packages

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

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Save 100% on your flight

$243

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 15 conference rooms on site, along with the valet parking and WiFi in public areas. Self parking, a lobby fireplace, and luggage storage are also offered.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$277

per person

Dec 15 - Dec 19

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.

Hampton Inn & Suites Chicago Medical District UIC

Near West Side

Save 100% on your flight

$302

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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.

Trump International Hotel & Tower Chicago

Downtown Chicago

$717

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$594

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.

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

$161 nightly

$189 total

Oct 2 - Oct 3

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

$190 nightly

$223 total

Oct 19 - Oct 20

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

$176 nightly

$207 total

Oct 2 - Oct 3

Total with 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

Hotel Chicago West Loop, SureStay Collection by Best Western

1622 W Jackson Blvd, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$163 total

Sep 28 - Sep 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

Hyatt House Chicago Medical/University District

1835 West Harrison Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$197 nightly

$231 total

Oct 5 - Oct 6

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

Hampton Inn & Suites Chicago Medical District UIC

710 S Seeley Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$196 total

Oct 2 - Oct 3

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

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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 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 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 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 $243. 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.