Far Southwest Side Vacation Packages 2025 from $300

Far Southwest Side flight + hotel vacation packages

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

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Save 100% on your flight

per person

Aug 22 - Aug 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 31 - Aug 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 22 - Aug 25

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.

La Banque Hotel

Save 100% on your flight

per person

Jul 8 - Jul 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

The Chicago Hotel Collection River North

Downtown Chicago

Save 100% on your flight

per person

Aug 28 - Sep 2

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Chicago (ORD)

A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A lobby fireplace, express check-out, and luggage storage are also on offer.

Top Far Southwest Side hotels deals

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

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

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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

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

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago, IL

Free Cancellation

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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 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.

Spa

Pet friendly

Fairmont Chicago at Millennium Park

200 North Columbus Drive, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

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A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified 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.

Spa

Pet friendly

Hotel Felix River North/Magnificent Mile

111 W Huron St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

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This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Pet friendly

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.

Popular places to visit

Dr. Percy Julian Residence

Find out about the history of Chicago when you take a trip to Dr. Percy Julian Residence. Make some time to visit the shops while you're in the area.

Final Call Newspaper Headquarters

Find out about the history of Chicago with a stop at Final Call Newspaper Headquarters.

Advocate High Tech Medical Center

Though Advocate High Tech Medical Center 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 Far Southwest Side?

With a Travelocity vacation package, you could paint the town red in Far Southwest Side for a mere $300. Flights, hotels and tours — we’re a one-stop shop for all of them. You can save some cash just for bundling together your bookings. And with everything taken care of before you even set off, you won’t have a care in the world.

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

Travelocity has endless ways to score an incredible Far Southwest Side package deal. Choose from as many as 400 airlines and 1,000,000 properties around the world and create a travel itinerary that’s right for you. With this amount of choice, now’s the time to book your next big adventure.

Why should I purchase my Far Southwest Side vacation bundle via Travelocity?

Travel is all about making fantastic new memories and leaving all your stresses behind — which is why we provide you with a professional team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you’ll always get the best price available on our terrific range of getaway packages. So what are you waiting for? There’s no time like the present to secure that vacation you’ve always dreamed of.

Can I save on my Far Southwest Side car rental if I book it with hotels and flights?

You sure can with our Far Southwest Side vacation packages. With one of these, there are lots of ways to make your vacation budget go further. Combine any two or more car, flight, hotel and tour bookings and see the savings grow. With your own ride, all the main sights in and around Far Southwest Side are a memorable road trip away.

Which airport is best for Far Southwest Side?

You’ll find there are three main options for those heading to and from Far Southwest Side — O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT).

What is there to do in Far Southwest Side?

Far Southwest Side has hidden gems at every turn, however ensure you plan a trip to Highland Community Bank and Carter G. Woodson Library while you’re in town. These two attractions are popular with visitors.