Southwest Side Vacation Packages 2025/2026 from $443

Southwest Side flight + hotel vacation packages

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

Waldorf Astoria Chicago

Downtown Chicago

Save 100% on your flight

$443

per person

Jan 24 - Jan 26

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the indoor pool and perks like a free area shuttle.

Art Villa

West Town

Save 100% on your flight

$711

per person

Feb 5 - Feb 9

found 15 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Chicago (ORD)

A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.

Hilton Chicago O'Hare Airport

O'Hare

Save 100% on your flight

$552

per person

Dec 31 - Jan 5

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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

$622

per person

Dec 25 - Dec 30

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

The Blackstone, Autograph Collection

Downtown Chicago

Save 100% on your flight

$546

per person

Dec 26 - Jan 2

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

This hotel features a restaurant, 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. Self parking, a lobby fireplace, and express check-in are also offered.

Top Southwest Side hotels deals

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$112 total

Nov 25 - Nov 26

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.

Pool

Breakfast included

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$115 total

Dec 7 - Dec 8

Total with taxes and fees

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Pet friendly

Free WiFi

citizenM Chicago Downtown

80 East Wacker Place Chicago IL

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$134 total

Nov 19 - Nov 20

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. A coffee shop, a communal living room, and express check-in are also on offer.

Free WiFi

Restaurant

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$149 total

Nov 24 - Nov 25

Total with taxes and fees

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 business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.

Pool

Spa

Warwick Allerton - Chicago

701 North Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$104 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. WiFi in public areas is free.

Free WiFi

Air conditioning

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$139 total

Dec 8 - Dec 9

Total with taxes and fees

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.

Breakfast included

Free WiFi

Don't see what you're looking for?

See all available properties in Southwest Side

View all properties

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

St. Bernard Hospital

Though St. Bernard Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Chicago while you are here.

Holy Cross Hospital

Though Holy Cross Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Chicago while you are here.

Marquette Park

4.5/5(2 reviews)

After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Frequently asked questions

How much are vacation packages to Southwest Side?

Epic adventures await in Southwest Side, with Travelocity vacation packages starting at just $443. Providing both hotels and flights, these sensational deals make it a cinch to see all corners of the globe.

Where can I get the best vacation package deals for Southwest Side?

It's simple — look no further than Travelocity. With no less than 400 partner airlines and 1,000,000 worldwide properties, it's easy to put together a Southwest Side package deal that suits your travel style.

Why should I purchase my Southwest Side vacation package with Travelocity?

Whether you're searching for the ultimate unplugged vacation or you crave the hustle and bustle of the big city, booking everything with Travelocity saves you time, hassle and money. No need to sift through hundreds of websites looking for the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our team of customer service experts are available 24/7 should you need anything at all.

Can I save on my Southwest Side car rental if I book it with my hotel or flight?

Sure can. And our Southwest Side vacation packages are the perfect way to do it. With only a few clicks you can save money as well as time by booking everything in one place. Collect the keys to your rental car and feel the freedom of the open road. Searching for things to do? Add some tours or experiences to your package and make savings on those too.

Which airport is best for Southwest Side?

For anyone heading to and from Southwest Side, the most used airports are O'Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT).

What is there to do in Southwest Side?

Southwest Side boasts hidden surprises at every corner, but be sure you plan a visit to both S.S. Peter and Paul Church and Balzekas Museum of Lithuanian Culture while you're here. These attractions are very popular with visitors to the region.