Southwest Side Vacation Packages 2025 from $817

Southwest Side flight + hotel vacation packages

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

Kimpton Gray Hotel by IHG

Downtown Chicago

Save 100% on your flight

per person

Sep 1 - Sep 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. A hair salon, WiFi in public areas, and luggage storage are also on offer.

Dorothy's

Lakeview

Save 100% on your flight

per person

Sep 1 - Sep 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Free WiFi in public areas, a communal living room, and luggage storage are available at this bed & breakfast. Enjoy the free continental breakfast each morning. Laundry facilities and a virtual front desk are also provided.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

per person

Sep 1 - Sep 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

per person

Sep 1 - Sep 8

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, laundry facilities, and concierge services are also on offer.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

per person

Sep 1 - Sep 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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.

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

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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

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave, Chicago, IL

Free Cancellation

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This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.

Pool

Spa

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

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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

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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

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

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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 Wade

644 N Lake Shore Dr, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-in are also provided.

Pool

Pet friendly

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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

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.

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.

Frequently asked questions

How much are vacation packages to Southwest Side?

Epic adventures await in Southwest Side, with Travelocity vacation packages starting at just $817. 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.