South Loop Vacation Packages 2025/2026 from $494

South Loop flight + hotel vacation packages

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

Renaissance Chicago Downtown Hotel

Downtown Chicago

Save 100% on your flight

per person

Sep 19 - Sep 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

The hotel's indoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A restaurant, laundry facilities, and concierge services are also provided.

The Langham, Chicago

Downtown Chicago

Save 100% on your flight

per person

Oct 2 - Oct 5

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. 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 laundry facilities.

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

per person

Sep 19 - Sep 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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 indoor pool, bar/lounge, and laundry facilities.

Waldorf Astoria Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 29 - Sep 3

found 4 hours ago

Roundtrip flight included

Atlanta (ATL) 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.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

per person

Sep 19 - Sep 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, 2 restaurants, and a gym are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.

Top South Loop hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$199 total

Aug 10 - Aug 11

Total includes 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

Travelodge by Wyndham Downtown Chicago

65 E Harrison St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$150 total

Aug 18 - Aug 19

Total includes taxes and fees

This hotel features a restaurant, a coffee shop, and free WiFi in public areas. Express check-out, luggage storage, and free newspapers are also on offer.

Free WiFi

Restaurant

Hilton Chicago

720 S Michigan Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$227 nightly

$266 total

Jul 26 - Jul 27

Total includes 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.

Hilton Garden Inn Chicago Downtown South Loop

55 E 11th Street, Chicago, IL

$142 nightly

$166 total

Aug 14 - Aug 15

Total includes taxes and fees

This hotel features a restaurant, 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 terrace, a snack bar/deli, and a free grocery shopping service are also on offer.

Sentral Michigan Avenue

808 SOUTH MICHIGAN AVENUE, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$211 nightly

$248 total

Aug 17 - Aug 18

Total includes taxes and fees

This aparthotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A garden, express check-in, and express check-out are also on offer.

Pool

Kitchen

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave, Chicago, IL

$281 nightly

$324 total

Jul 24 - Jul 25

Total includes taxes and fees

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

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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

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Shedd Aquarium

Make time in your itinerary to visit the sea life you'll find at Shedd Aquarium during your visit to Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

Frequently asked questions

How much are vacation packages to South Loop?

Starting from as little as $494, hotel and flight packages are an ideal way to stretch your vacation budget even further. South Loop, here you come!

Where can I get the best vacation package deals for South Loop?

You'll find a terrific selection of South Loop package deals on Travelocity. With no less than 400 air carriers and 1,000,000 worldwide properties, piecing together a dream getaway will be a breeze.

Why should I book my South Loop vacation package with Travelocity?

Incredible savings, an abundance of exciting destinations and a team of customer service experts available 24/7 — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always score the best possible deal with Travelocity.

Will I save money on my South Loop car rental if I combine it with hotels and flights?

Booking a South Loop vacation package with Travelocity is one of the best ways to save your time and money. You can combine a car, flight and hotel, or any combination of them, and land awesome discounts. You might also like to throw in some tours and experiences. After you've picked up the keys to your rental car, head out of the neighborhood and see what the area has to offer. About 40 mi from South Loop, Six Flags Great America is worth a road trip.

What is there to do in South Loop?

Soldier Field and Field Museum of Natural History have captivated so many visitors. Check these sights off your itinerary and find out what the hype is about.