When is the best time to go to East Side?

The best time to visit East Side, Illinois is typically during the late spring (May to early June) or early autumn (September to October) when the weather is most pleasant. During these months, you'll find comfortable temperatures, generally ranging from 15°C to 25°C, which are ideal for exploring the area's outdoor attractions and enjoying local events without the extreme heat of summer or the chill of winter. The foliage in autumn can be quite lovely, adding to the scenic appeal. For those interested in outdoor activities like hiking or cycling along the Mississippi River, these seasons offer the most agreeable conditions.

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 to 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 East Side hotel for you.

How can I save on a hotel booking in East Side with Expedia?

One Key™ —Expedia’s free travel rewards program—gives you instant access to discounts with Member Prices on East Side hotels. Plus, you’ll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in East Side?

Hotel prices in East Side 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.

East Side Hotels: Cheap Accommodation in East Side

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Our top choices for East Side hotels

A modern dining area with round tables and white chairs, a kitchen area with a coffee machine, and a view of the outdoors through large windows.

1. Hilton Vacation Club Hotel Blake Chicago

The Loop, 20.3 km from East Side

John

includes taxes & fees

3 Nov - 4 Nov

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

2. Fairmont Chicago at Millennium Park

The Loop, 21.2 km from East Side

Ruby

includes taxes & fees

31 Oct - 1 Nov

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

3. Swissotel - Chicago

21.3 km from East Side

Michael

includes taxes & fees

31 Oct - 1 Nov

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

4. Hilton Chicago

The Loop, 19.9 km from East Side

Alan

includes taxes & fees

30 Oct - 31 Oct

A snack bar with various packaged snacks and beverages.

5. Cambria Hotel Chicago Loop - Theatre District

Theatre District, 21.2 km from East Side

Sai Sudarshan

includes taxes & fees

1 Nov - 2 Nov

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

6. Best Western Grant Park Hotel

The Loop, 19.5 km from East Side

Shelby Ryann

includes taxes & fees

1 Nov - 2 Nov

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

7. Central Loop Hotel

Theatre District, 20.8 km from East Side

Nathan

includes taxes & fees

1 Nov - 2 Nov

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

8. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 21.8 km from East Side

Poua

includes taxes & fees

1 Nov - 2 Nov

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

9. Congress Plaza Hotel

The Loop, 20.1 km from East Side

Guadalupe

includes taxes & fees

4 Nov - 5 Nov

10. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Streeterville, 22.6 km from East Side

Anand

includes taxes & fees

2 Nov - 3 Nov

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

11. ACME Hotel Chicago, Outset Collection by Hilton

River North, 22 km from East Side

Gabriela

includes taxes & fees

1 Nov - 2 Nov

12. Hampton Inn Chicago Downtown/N Loop/Michigan Ave

Theatre District, 21.4 km from East Side

Jeanvia

includes taxes & fees

2 Nov - 3 Nov

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

13. Travelodge by Wyndham Downtown Chicago

The Loop, 20.1 km from East Side

Sandra

includes taxes & fees

2 Nov - 3 Nov

A long dining table with chairs, overhead lighting, and a marble wall with a decorative ceiling.

14. Palmer House a Hilton Hotel

Theatre District, 20.8 km from East Side

Gabriella

includes taxes & fees

31 Oct - 1 Nov

A restaurant interior with brick walls, hanging spherical light fixtures, and a visible kitchen area.

15. Arlo Chicago

Theatre District, 21.2 km from East Side

Ashley Nacole

includes taxes & fees

1 Nov - 2 Nov

A conference room with a long table, chairs, a projector screen, and a carpeted floor.

16. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 22 km from East Side

Nadine Georgette

includes taxes & fees

1 Nov - 2 Nov

17. Club Quarters Hotel, Central Loop, Chicago

Theatre District, 20.8 km from East Side

Synova

includes taxes & fees

1 Nov - 2 Nov

A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

18. L7 Chicago by LOTTE

Theatre District, 21.4 km from East Side

Emily

includes taxes & fees

1 Nov - 2 Nov

A hotel with a modern glass facade, a prominent Hampton Inn sign, and a Homewood Suites by Hilton sign.

19. Hampton Inn Chicago Downtown/Magnificent Mile

Streeterville, 22.1 km from East Side

William

includes taxes & fees

1 Nov - 2 Nov

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

20. Hyatt Regency Chicago

The Loop, 21.4 km from East Side

Mark

includes taxes & fees

31 Oct - 1 Nov

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Our guide on where to stay in East Side

Find the best East Side areas for the activities you enjoy most. Learn more about East Side

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

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

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

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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Top East Side Hotel Reviews

Recent Reviews in East Side

Congress Plaza Hotel

10/10 Excellent

"Room was clean, staff were friendly and the bar was relaxing."

Freehand Chicago

10/10 Excellent

"We absolutely enjoyed our stay at the Kins Hotel. Our room was exceptionally clean, spacious and comfortable, and it was actually much larger than the images we had seen when booking, which was a lovely surprise. The staff were amazing and couldn’t have been more helpful or friendly. From the reception staff and valet team to the cleaners, everyone was welcoming, professional and always happy to assist whenever we had a question. Overall, we had a fantastic stay at the Kins Hotel and wouldn’t hesitate to recommend it to anyone looking for a great place to stay. We would happily return ourselves!"

East Side Hotels, Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for East Side hotels

1. Hilton Vacation Club Hotel Blake Chicago

2. Fairmont Chicago at Millennium Park

3. Swissotel - Chicago

4. Hilton Chicago

5. Cambria Hotel Chicago Loop - Theatre District

6. Best Western Grant Park Hotel

7. Central Loop Hotel

8. DoubleTree by Hilton Chicago - Magnificent Mile

9. Congress Plaza Hotel

10. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

11. ACME Hotel Chicago, Outset Collection by Hilton

12. Hampton Inn Chicago Downtown/N Loop/Michigan Ave

13. Travelodge by Wyndham Downtown Chicago

14. Palmer House a Hilton Hotel

15. Arlo Chicago

16. Courtyard by Marriott Chicago Magnificent Mile

17. Club Quarters Hotel, Central Loop, Chicago

18. L7 Chicago by LOTTE

19. Hampton Inn Chicago Downtown/Magnificent Mile

20. Hyatt Regency Chicago

Our guide on where to stay in East Side

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top East Side Hotel Reviews

Recent Reviews in East Side

Congress Plaza Hotel

Frequently asked questions

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