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?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in East Side.

How much is the nightly rate at a East Side hotel?

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.

The Best Hotels in East Side, Chicago - 2026 Updated Prices

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Our top choices for East Side hotels

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

1. Congress Plaza Hotel

The Loop, 12.5 mi from East Side

Ashya

includes taxes & fees

11 Nov - 12 Nov

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

2. Best Western Grant Park Hotel

The Loop, 12.1 mi from East Side

Colin

includes taxes & fees

10 Nov - 11 Nov

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

3. The Wade

Streeterville, 13.6 mi from East Side

Erin

includes taxes & fees

12 Nov - 13 Nov

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

4. Travelodge by Wyndham Downtown Chicago

The Loop, 12.5 mi from East Side

Sandra

includes taxes & fees

11 Nov - 12 Nov

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

5. L7 Chicago by LOTTE

Theatre District, 13.3 mi from East Side

Jeffrey Thomas

includes taxes & fees

1 Nov - 2 Nov

The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

6. Claridge House Chicago, Tapestry Collection by Hilton

14.6 mi from East Side

Scott

includes taxes & fees

9 Nov - 10 Nov

A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

7. Hilton Vacation Club Hotel Blake Chicago

The Loop, 12.6 mi from East Side

Mario

includes taxes & fees

3 Nov - 4 Nov

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

8. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 12.1 mi from East Side

Aran

includes taxes & fees

9 Nov - 10 Nov

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

9. Hilton Chicago

The Loop, 12.3 mi from East Side

Anna

includes taxes & fees

30 Oct - 31 Oct

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

10. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 13.6 mi from East Side

Poua

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with a glass ceiling, multiple seating areas, and city views.

11. Hilton Garden Inn Chicago Downtown/Magnificent Mile

River North, 13.6 mi from East Side

Hakeim

includes taxes & fees

1 Nov - 2 Nov

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

12. Silversmith Hotel Chicago Downtown

Theatre District, 13 mi from East Side

Guy

includes taxes & fees

15 Nov - 16 Nov

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

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

Streeterville, 13.2 mi from East Side

Shanequa

includes taxes & fees

12 Nov - 13 Nov

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

14. Hotel 505 River North

River North, 13.6 mi from East Side

Giana

includes taxes & fees

15 Nov - 16 Nov

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

15. The Whitehall Hotel, BW Premier Collection

Streeterville, 14.1 mi from East Side

KURT

includes taxes & fees

2 Nov - 3 Nov

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

16. Arlo Chicago

Theatre District, 13.2 mi from East Side

Pam

includes taxes & fees

2 Nov - 3 Nov

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

Theatre District, 13.3 mi from East Side

Fm

includes taxes & fees

1 Nov - 2 Nov

A historic building with a glass entrance, large columns, and decorative planters with flowers.

18. Warwick Allerton - Chicago

Streeterville, 13.8 mi from East Side

Nelza

includes taxes & fees

11 Nov - 12 Nov

An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

19. Palmer House a Hilton Hotel

Theatre District, 12.9 mi from East Side

Christy

includes taxes & fees

31 Oct - 1 Nov

A high-rise hotel with a prominent curved glass facade, multiple floors, and a visible "EMBASSY" sign.

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 13.5 mi from East Side

jaimie

includes taxes & fees

1 Nov - 2 Nov

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Where to stay in East Side

Find the best East Side areas 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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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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

L7 Chicago by LOTTE

10/10 Excellent

"We loved this hotel. The room was spacious, modern, and so well appointed. So many hip hotels disappoint with their space but between the places for clothes, the super comfy bed, the robes, and everything else, this felt like modern luxury. The staff were terrific. And the location made it easy to get anywhere."

Fairmont Chicago at Millennium Park

10/10 Excellent

"I chose this hotel for its close proximity to the Chicago Marathon starting line, it couldn't have been a more perfect location. The hotel check was easy and the rooms were clean, comfortable for our needs. We were able to leave our luggage with the front desk upon check out on Marathon day as we were flying home after the race but had to check out the morning of the race. My only issue was the extremely high price for the weekend but that is my own fault for not booking earlier once deciding to enter the race, I assume the cost would have been much lower if I had booked more in advance but hindsight - 20-20 .A great weekend and a lovely hotel."

Hotel Saint Clair- Magnificent Mile

8/10 Good

"this hotel has been around for many years and is definitely a bit tired. The lobby is extremely small and could use sprucing up in some expansion. The elevators need a pass to go to the floor, which I totally agree with but that sad there is no or appears to be no freight elevator for staff to use as a result you have staff doing functions and guests trying to get to their room. Nothing wrong with the hotel. It just needs some renovation. Location wise cannot beat it. It’s in a fabulous location and very convenient to everything."

Search Hotels in East Side, Chicago

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Our top choices for East Side hotels

1. Congress Plaza Hotel

2. Best Western Grant Park Hotel

3. The Wade

4. Travelodge by Wyndham Downtown Chicago

5. L7 Chicago by LOTTE

6. Claridge House Chicago, Tapestry Collection by Hilton

7. Hilton Vacation Club Hotel Blake Chicago

8. Hilton Garden Inn Chicago Downtown South Loop

9. Hilton Chicago

10. DoubleTree by Hilton Chicago - Magnificent Mile

11. Hilton Garden Inn Chicago Downtown/Magnificent Mile

12. Silversmith Hotel Chicago Downtown

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

14. Hotel 505 River North

15. The Whitehall Hotel, BW Premier Collection

16. Arlo Chicago

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

18. Warwick Allerton - Chicago

19. Palmer House a Hilton Hotel

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Where to stay in East Side

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top East Side Hotel Reviews

L7 Chicago by LOTTE

Frequently asked questions

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