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

A cityscape with a mix of modern and older buildings, a large body of water in the background, and a clear sky.

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Our top choices for South Shore hotels

A large, historic building with a central courtyard surrounded by trees.

1. Hilton Chicago

The Loop, 13.1 km from South Shore

Alan

CA $312 total

includes taxes & fees

Oct 24 - Oct 25

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

2. Congress Plaza Hotel

The Loop, 13.3 km from South Shore

John

CA $270 total

includes taxes & fees

Oct 26 - Oct 27

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

3. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 12.7 km from South Shore

Aran

CA $313 total

includes taxes & fees

Oct 25 - Oct 26

A modern hotel lobby with a large sign reading "THE WADE," a spacious area with a patterned floor, large windows offering views, and potted plants.

4. The Wade

Streeterville, 15.1 km from South Shore

Fernanda

CA $251 total

includes taxes & fees

Oct 25 - Oct 26

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

Tremecka

CA $259 total

includes taxes & fees

Oct 25 - Oct 26

A restaurant with booths and tables, a television on the wall, and a view of the street outside.

6. Hilton Vacation Club Hotel Blake Chicago

The Loop, 13.4 km from South Shore

John

CA $531 total

includes taxes & fees

Oct 14 - Oct 15

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

7. Club Quarters Hotel, Central Loop, Chicago

Theatre District, 14 km from South Shore

Julian

CA $249 total

includes taxes & fees

Oct 25 - Oct 26

A spacious lobby with a central coffee table, sofas, and a large mirror.

8. The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 16.7 km from South Shore

Marta

CA $301 total

includes taxes & fees

Oct 14 - Oct 15

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

9. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 12.7 km from South Shore

Cecilia

CA $352 total

includes taxes & fees

Oct 25 - Oct 26

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

10. Carleton of Oak Park

23.5 km from South Shore

Suzanne

CA $175 total

includes taxes & fees

Oct 6 - Oct 7

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

11. Hilton Chicago/Magnificent Mile Suites

Streeterville, 15.9 km from South Shore

Brian

CA $294 total

includes taxes & fees

Oct 25 - Oct 26

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

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

Streeterville, 14.7 km from South Shore

Shanequa

CA $583 total

includes taxes & fees

Oct 22 - Oct 23

13. The Allegro Royal Sonesta Hotel Chicago Loop

Theatre District, 14.6 km from South Shore

Kurt

CA $333 total

includes taxes & fees

Oct 25 - Oct 26

A cozy room with a sofa, a dining table, and a window with a view of buildings.

14. LIVN - West Loop Chicago

14.1 km from South Shore

chidubem

CA $365 total

includes taxes & fees

Oct 1 - Oct 2

A multi-story hotel with a prominent sign reading "Crowne Plaza."

15. Crowne Plaza Chicago West Loop by IHG

14.6 km from South Shore

Phillip

CA $317 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a sofa, a small table, a desk with a chair, a bed, a TV, and a window with curtains.

16. Silversmith Hotel Chicago Downtown

Theatre District, 14.1 km from South Shore

Carmen

CA $376 total

includes taxes & fees

Oct 25 - Oct 26

17. Central Loop Hotel

Theatre District, 14 km from South Shore

Nathan

CA $249 total

includes taxes & fees

Oct 25 - Oct 26

A grand lobby with a central bar, high ceilings, and classical architecture.

18. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Theatre District, 14.1 km from South Shore

Amanda

CA $335 total

includes taxes & fees

Oct 4 - Oct 5

A street view with a row of parked cars, a building with a sign reading "SONDE," and another sign that says "Diamonds On Parade."

19. LIVN - Millennium Park Downtown Chicago

Theatre District, 14 km from South Shore

Rebecca

CA $378 total

includes taxes & fees

Oct 1 - Oct 2

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

20. River Hotel

The Loop, 14.7 km from South Shore

Jared

CA $313 total

includes taxes & fees

Oct 25 - Oct 26

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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

Hilton Chicago

10/10 Excellent

"Great stay! Everyone was so nice from check in with Joao until we walked out the doors."

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Room was very clean and comfortable. Great bed, nice shower. Only stayed one night. It was nice having coffee in the room and a Starbucks downstairs. There were also plenty of restaurants within walking distance. We did not eat breakfast at the hotel as it was a very expensive buffet. We didn’t have a chance to walk around since our visit was short and the weather was terrible but it looked like it was a very convenient location close to Navy Pier and other attractions."

Hyatt Regency Chicago

10/10 Excellent

"The room was very clean and attractive. My only suggestion is that bars for safety, in the bathroom would be helpful, when entering the tub for a bath or shower. Everyone with whom I had contact was professional and eager to assist. It was a delight to deal with staff. My only suggestion is that on the day I was leaving, the cleaning staff appeared to rush me out at 9:00 in the morning, when I had until 12 to check out. That was somewhat annoying. Other than that, it was a very pleasant experience and I would return to this hotel in the future."

Hotels in South Shore, Chicago

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Our top choices for South Shore hotels

1. Hilton Chicago

2. Congress Plaza Hotel

3. Hilton Garden Inn Chicago Downtown South Loop

4. The Wade

5. Travelodge by Wyndham Downtown Chicago

6. Hilton Vacation Club Hotel Blake Chicago

7. Club Quarters Hotel, Central Loop, Chicago

8. The Chicago Hotel Collection Ambassador Gold Coast

9. Homewood Suites by Hilton Chicago Downtown South Loop

10. Carleton of Oak Park

11. Hilton Chicago/Magnificent Mile Suites

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

13. The Allegro Royal Sonesta Hotel Chicago Loop

14. LIVN - West Loop Chicago

15. Crowne Plaza Chicago West Loop by IHG

16. Silversmith Hotel Chicago Downtown

17. Central Loop Hotel

18. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

19. LIVN - Millennium Park Downtown Chicago

20. River Hotel

Where to stay in South Shore

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top South Shore Hotel Reviews

Hilton Chicago

Frequently asked questions

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