Title: East Side Holidays 2026 from £892 | Expedia.co.uk

[Hotels in East Side](https://expedia.co.uk/East-Side-Chicago-Hotels.0-n6129881-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[East Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-East-Side.d6129881.Car-Hire-Guide)

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# East Side Holidays from £892

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to £335 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Packages with flights are ATOL protected

### Your East Side Holiday

Book a customized East Side holiday package and enjoy the delights of this neighbourhood from morning till evening. From its nature and walking to its unique personality and vibe, there's an endless list of reasons to visit East Side. Some top nearby attractions to visit during your trip to East Side include [Calumet Park](https://www.expedia.co.uk/Calumet-Park-East-Side.d553248621555594792.Attraction), [Calumet Beach](https://www.expedia.co.uk/Calumet-Beach-Chicago.d553248635983994343.Attraction) and [Bronzeville Childrens Museum](https://www.expedia.co.uk/Bronzeville-Childrens-Museum-Calumet-Heights.d6227657.Attraction). Stop dreaming and start doing. When you're ready to book your next holiday to East Side, Expedia will help get you there.

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

![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Wade

Downtown Chicago

£892

per person

27 Apr - 2 May

found 11 hours ago

Return direct flight included

London (LGW) to Chicago (ORD)

8.4/10 Very Good! (1,444 reviews)

I had a great stay at the Wade Hotel in Chicago! The room was very clean and comfortable, and the staff was friendly, professional, and welcoming from check-in to check-out. The amenities were convenient, and the location made it easy to get around the city. I would definitely stay here again and recommend it to anyone visiting Chicago.

Reviewed on 9 Feb 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

£1,000

per person

27 Apr - 2 May

found 11 hours ago

Return direct flight included

London (LGW) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Friendly staff, tasteful room

Reviewed on 11 Feb 2026

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

£937

per person

27 Apr - 2 May

found 11 hours ago

Return direct flight included

London (LGW) to Chicago (ORD)

9.2/10 Wonderful! (347 reviews)

Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.

Reviewed on 9 Feb 2026

![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Virgin Hotels Chicago

Downtown Chicago

£1,068

per person

27 Apr - 2 May

found 11 hours ago

Return direct flight included

London (LGW) to Chicago (ORD)

9.2/10 Wonderful! (1,404 reviews)

Great staff- very friendly

Reviewed on 9 Feb 2026

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

£1,080

per person

21 Apr - 28 Apr

found 1 day ago

Return direct flight included

Manchester (MAN) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on 2 Feb 2026

## Where to stay in East Side

Find the best East Side areas and neighborhoods for the activities you enjoy most. [Learn more about East Side](https://expedia.co.uk/Chicago-East-Side.dx6129881)

![Downtown Chicago featuring a city](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown Chicago

4 out of top 10 points of interest in this area

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

[Find hotels in Downtown Chicago](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=6350699)

![Magnificent Mile - River North](https://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Magnificent Mile

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

[Find hotels in Magnificent Mile](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=800025)

![The Loop - Downtown featuring a river or creek](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### The Loop

4.5/5(187 area reviews)

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

[Find hotels in The Loop](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=800024)

![River North showing railway items, street scenes and a city](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotels in River North](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=6350695)

![Underground passage in the Chicago O'Hare airport](https://images.trvl-media.com/place/553248635074842747/1dda5453-2f05-4485-9f3c-404a7075d270.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### O'Hare

3.5/5(10 area reviews)

 Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago. 

[Find hotels in O'Hare](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=553248635074842747)

## Top hotels in East Side

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

£77

12 Feb - 13 Feb

includes taxes & fees

8/10 Very Good! (9,876 reviews)

Staff was great, room service was quick and affordable. Room was spotless.

Reviewed on 10 Feb 2026

[](https://expedia.co.uk/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=6129881)

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Fully refundableReserve now, pay when you stay

£122

4 Mar - 5 Mar

includes taxes & fees

9.2/10 Wonderful! (3,313 reviews)

Love the room! Very ritzy!!

Reviewed on 8 Feb 2026

[](https://expedia.co.uk/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true&regionId=6129881)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Fully refundableReserve now, pay when you stay

£88

22 Feb - 23 Feb

includes taxes & fees

8.4/10 Very Good! (5,643 reviews)

Positives- As my friend said as we went to breakfast “the people here are so nice and look happy to work here!” I agree! Eloisa (I hope that is correct-our bartender ) made happy hour on Friday night even happier! She was friendly and knowledgeable, suggesting drinks we hadn’t had before just by ...

Reviewed on 8 Feb 2026

[](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=6129881)

[See all 4,304 properties in East Side](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&regionId=6129881)

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.

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All Inclusive Holidays

[](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Holidays

[](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Friendly Holidays

[](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Holidays

[](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Holidays

[](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click)

![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ+ Holidays

[](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Holidays

[](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Holidays

[](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Pet Friendly Holidays

[](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click)

![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click)

## Frequently asked questions

### How much does an East Side travel package cost?

### If I'm not able to travel, can I cancel my East Side travel package?

### How do I get a cheap travel package to East Side?

### Does Expedia offer Book Now, Pay Later East Side holidays?

> - Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams come true.
> - Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your holiday in multiple transactions.
> - Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan with Klarna.

### Where should I stay in East Side?

### What are the top hotels in East Side?

### How far in advance should I book my East Side holiday?

### What does an Expedia East Side travel package include?

### What should I know before booking an East Side travel package?

### Can I choose my airline with an East Side Expedia travel package?

### Popular places to visit

![Wrigley Field featuring a city, a sporting event and city views](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

[](https://expedia.co.uk/Wrigley-Field-Lakeview.d6034754.Attraction)

![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. 

[](https://expedia.co.uk/Michigan-Avenue-Downtown-Chicago.d6156167.Attraction)

![Navy Pier featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

[](https://expedia.co.uk/Navy-Pier-Downtown-Chicago.d6069215.Attraction)

### Things to do

![Chicago: Navy Pier Centennial Wheel Regular & Express Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago: Navy Pier Centennial Wheel Ticket

£18

per adult

**88%** of travellers recommend

[](https://expedia.co.uk/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.activity-details)

![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Flyover in Chicago

£28

per adult

**98%** of travellers recommend

[](https://expedia.co.uk/things-to-do/flyover-in-chicago.a50023979.activity-details)

![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wendella's 90-min Chicago River Architecture Tour

£30

per adult

**94%** of travellers recommend

[](https://expedia.co.uk/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details)

[See all activities in Chicago](https://expedia.co.uk/things-to-do/search?rid=6129881)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.