Southwest Side Vacation Packages 2026 from $594

Southwest Side flight + hotel vacation packages

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

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$594

per person

Nov 1 - Nov 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant and a 24-hour gym are featured at this hotel. 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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$860

per person

Oct 28 - Nov 3

found 1 day 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$726

per person

Nov 1 - Nov 4

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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$704

per person

Nov 1 - Nov 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This 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, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$1,424

per person

Oct 5 - Oct 9

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.

Top Southwest Side hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$133 total

Sep 8 - Sep 9

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.

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$170 total

Aug 31 - Sep 1

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.

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

Get rates

A gym, self parking, and a virtual front desk are featured at this aparthotel. WiFi in public areas is free. A convenience store and luggage storage are also provided.

River Hotel

75 East Wacker Drive Chicago IL

Free Cancellation

Reserve now, pay when you stay

$137 nightly

$163 total

Aug 30 - Aug 31

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.

The Allegro Royal Sonesta Hotel Chicago Loop

171 W Randolph St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$221 nightly

$263 total

Sep 27 - Sep 28

Total with taxes and fees

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

Fairmont Chicago at Millennium Park

200 North Columbus Drive Chicago IL

Free Cancellation

Reserve now, pay when you stay

$269 nightly

$320 total

Sep 8 - Sep 9

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

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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.

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Frequently asked questions

How much are vacation packages to Southwest Side?

Epic adventures await in Southwest Side, with Travelocity vacation packages starting at just $594. 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.