When is the best time to go to South Shore?

The best time to go to South Shore is during the summer months, from June to August, when the weather is warm and ideal for enjoying the region's outdoor attractions. This period offers long, sunny days great for exploring the Indiana Dunes National Park, which stretches along Lake Michigan. You'll find plenty of opportunities for hiking, swimming, and relaxing on the beaches. The lake's waters are at their most inviting during these months. Couples often find summer particularly appealing for romantic strolls along the shore at sunset or enjoying outdoor dining in towns like Chesterton. The pleasant evenings are great for experiencing local festivals and events that often take place during this season. Families with children will also appreciate the summer for its extensive range of outdoor activities. The warmer temperatures mean kids can spend hours playing in the sand and splashing in Lake Michigan without getting cold.

Can I cancel my hotel reservation on Expedia?

Many Expedia hotel reservations are refundable, provided that you cancel before the hotel’s cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right South Shore hotel for you.

How much is the nightly rate at a South Shore hotel?

Hotel prices in South Shore often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

10 Best Hotels in South Shore, Chicago for 2026

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Our top choices for South Shore hotels

A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

1. Hilton Chicago

The Loop, 13.1 km from South Shore

Anna

CA $323 total

includes taxes & fees

Oct 30 - Oct 31

A modern interior with a bar area, seating, and decorative wooden panels.

2. Best Western Grant Park Hotel

The Loop, 12.7 km from South Shore

Shelby Ryann

CA $272 total

includes taxes & fees

Oct 26 - Oct 27

A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.

3. Hilton Vacation Club Hotel Blake Chicago

The Loop, 13.4 km from South Shore

John

CA $307 total

includes taxes & fees

Oct 29 - Oct 30

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

4. Congress Plaza Hotel

The Loop, 13.3 km from South Shore

Katimah

CA $196 total

includes taxes & fees

Nov 2 - Nov 3

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

5. Travelodge by Wyndham Downtown Chicago

The Loop, 13.3 km from South Shore

Sandra

CA $185 total

includes taxes & fees

Nov 2 - Nov 3

A modern kitchen with a large window, a dining area, and a view of the sea.

6. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 12.7 km from South Shore

Jayne

CA $308 total

includes taxes & fees

Oct 25 - Oct 26

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

7. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 12.7 km from South Shore

Aran

CA $311 total

includes taxes & fees

Oct 25 - Oct 26

A bar area with a checkered floor, leather seating, and a bar counter with a visible liquor selection.

8. ACME Hotel Chicago, Outset Collection by Hilton

River North, 15.2 km from South Shore

alex

CA $235 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

9. Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 14.7 km from South Shore

Shanequa

CA $437 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with a marble island, fruit bowls, and a city view.

10. Fairmont Chicago at Millennium Park

The Loop, 14.4 km from South Shore

Ruby

CA $366 total

includes taxes & fees

Oct 31 - Nov 1

A modern building with large glass windows and a covered walkway.

11. Palmer House a Hilton Hotel

Theatre District, 14 km from South Shore

Sydney

CA $365 total

includes taxes & fees

Oct 31 - Nov 1

A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

12. Club Quarters Hotel, Central Loop, Chicago

Theatre District, 14 km from South Shore

hermon

CA $220 total

includes taxes & fees

Nov 1 - Nov 2

13. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Streeterville, 15.9 km from South Shore

Anand

CA $184 total

includes taxes & fees

Nov 2 - Nov 3

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

14. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 15.1 km from South Shore

Poua

CA $214 total

includes taxes & fees

Nov 2 - Nov 3

A snack bar with various packaged snacks and beverages.

15. Cambria Hotel Chicago Loop - Theatre District

Theatre District, 14.4 km from South Shore

Vansh

CA $243 total

includes taxes & fees

Nov 1 - Nov 2

A dining table set for six with a cityscape view through large windows.

16. Swissotel - Chicago

14.5 km from South Shore

Hilary

CA $409 total

includes taxes & fees

Oct 31 - Nov 1

A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

17. Silversmith Hotel Chicago Downtown

Theatre District, 14.1 km from South Shore

Haesung

CA $288 total

includes taxes & fees

Nov 2 - Nov 3

A bar area with a long counter, bar stools, and a mirrored wall.

18. The Whitehall Hotel, BW Premier Collection

Streeterville, 15.9 km from South Shore

KURT

CA $201 total

includes taxes & fees

Nov 2 - Nov 3

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

19. Hyatt House Chicago/West Loop-Fulton Market

15.2 km from South Shore

Joel

CA $327 total

includes taxes & fees

Nov 1 - Nov 2

20. Hampton Inn Majestic Chicago Theatre District

Theatre District, 14.1 km from South Shore

Michael

CA $255 total

includes taxes & fees

Nov 2 - Nov 3

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Where to stay in South Shore

Find the best South Shore areas and neighborhoods for the activities you enjoy most.

A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

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A large, historic building with a central tower and multiple windows, located near a body of water.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

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A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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Top South Shore Hotel Reviews

Fairmont Chicago at Millennium Park

10/10 Excellent

"Well appointed rooms, kind staff, and very responsive"

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"CQ is a reliable brand as this property demonstrated. I was particularly pleased with the size of the room and fitness facility. Best CQ I have stayed at and would return. Two quibbles: No desk lamp, therefore a dark work area and no hand soap (use body gel? I bring my own). Housekeeping excellent."

Hotels in South Shore, Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for South Shore hotels

1. Hilton Chicago

2. Best Western Grant Park Hotel

3. Hilton Vacation Club Hotel Blake Chicago

4. Congress Plaza Hotel

5. Travelodge by Wyndham Downtown Chicago

6. Homewood Suites by Hilton Chicago Downtown South Loop

7. Hilton Garden Inn Chicago Downtown South Loop

8. ACME Hotel Chicago, Outset Collection by Hilton

9. Sable at Navy Pier Chicago, Curio Collection by Hilton

10. Fairmont Chicago at Millennium Park

11. Palmer House a Hilton Hotel

12. Club Quarters Hotel, Central Loop, Chicago

13. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

14. DoubleTree by Hilton Chicago - Magnificent Mile

15. Cambria Hotel Chicago Loop - Theatre District

16. Swissotel - Chicago

17. Silversmith Hotel Chicago Downtown

18. The Whitehall Hotel, BW Premier Collection

19. Hyatt House Chicago/West Loop-Fulton Market

20. Hampton Inn Majestic Chicago Theatre District

Where to stay in South Shore

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top South Shore Hotel Reviews

Fairmont Chicago at Millennium Park

Frequently asked questions

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