Southwest Side Vacation Packages 2026 from $406

Southwest Side flight + hotel vacation packages

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

The Glen Club

Save 100% on your flight

$406

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Chicago (ORD)

A golf course and a restaurant are featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$976

per person

Nov 28 - Dec 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$865

per person

Nov 25 - Nov 28

found 2 days 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 – Old Town

Downtown Chicago

Save 100% on your flight

$582

per person

Dec 10 - Dec 14

found 13 hours ago

Roundtrip flight included

Philadelphia (PHL) 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.

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight

$493

per person

Nov 13 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

Top Southwest Side hotels deals

River Hotel

75 East Wacker Drive Chicago IL

Free Cancellation

Reserve now, pay when you stay

$186 nightly

$221 total

Oct 25 - Oct 26

Total with taxes and fees

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.

Pet friendly

Free WiFi

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$157 nightly

$187 total

Oct 26 - Oct 27

Total with taxes and fees

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.

Free WiFi

Restaurant

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$213 total

Oct 25 - Oct 26

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, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.

Pet friendly

Free WiFi

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$213 total

Oct 25 - Oct 26

Total with taxes and fees

This boutique 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, express check-out, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and wedding services.

Pet friendly

Free WiFi

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$206 nightly

$245 total

Oct 25 - Oct 26

Total with taxes and fees

This hotel features free WiFi in public areas, laundry facilities, and valet parking. Enjoy the free continental breakfast each morning. Express check-in, express check-out, and a computer station are also on offer.

Breakfast included

Pet friendly

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$188 nightly

$221 total

Oct 24 - Oct 25

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Pool

Hot Tub

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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.

Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 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.

See properties

Frequently asked questions

How much are vacation packages to Southwest Side?

Epic adventures await in Southwest Side, with Travelocity vacation packages starting at just $406. 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.