East Side Holidays from £1,077

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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, Calumet Beach and Bronzeville Childrens Museum. 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,537, price is now £1,077 per person
£1,077
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
This was a great price for a great stay!! Central to many locations downtown! I am planning to book this hotel again in the future!

Reviewed on 9 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,898, price is now £1,243 per person
£1,243
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago

Reviewed on 10 Apr 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,789, price is now £1,226 per person
£1,226
per person
17 Jun - 21 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The place was beautiful. Breakfast was lovely and I enjoyed everything.

Reviewed on 10 Apr 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was £1,964, price is now £1,357 per person
£1,357
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Very friendly staff, great location.

Reviewed on 6 Apr 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,725, price is now £1,224 per person
£1,224
per person
11 May - 18 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Well located, friendly, helpful staff, clean and well appointed.

Reviewed on 10 Apr 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
Downtown Chicago

Downtown Chicago

5 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

Top hotels in East Side

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £101 per night from 26 Apr to 27 Apr
£101
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,079 reviews)
Parking was terrible and extremely expensive

Reviewed on 10 Apr 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is £120 per night from 26 Apr to 27 Apr
£120
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,095 reviews)
No complaints. Everyone went above and beyond to accommodate our party and luggage. Thank you to Hussan. He made the stay more enjoyable.

Reviewed on 10 Apr 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £136 per night from 19 Apr to 20 Apr
£136
19 Apr - 20 Apr
includes taxes & fees
8.6/10 Excellent! (5,831 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...

Reviewed on 9 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,285 properties in East Side
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an East Side travel package cost?
Browse and book everything in one place with our East Side travel packages, which start from only £1,077. Choose the flights and hotels that suit your travel plans. Then, add on one or two sightseeing tours to round off your unique escape.
If I'm not able to travel, can I cancel my East Side travel package?
If your holiday plans in East Side have changed, it's good to know that you can cancel or amend your booking. If you made your booking within the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose fees. For more information, check our Customer Service Portal.
How do I get a cheap travel package to East Side?
Find flights that fit in with your schedule, add a hotel room to your booking and watch the savings rack up with an East Side travel package. It's as simple as that! From flights and hotels to activities and rental cars, Expedia makes travelling cheap and easy. And with over 550 airlines and 1,000,000 hotel options globally to choose from, you'll never be short of choice.
Does Expedia offer Book Now, Pay Later East Side holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has come up with a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book a dream getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your break. Check out these flexible payment options:

  • 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?
Make sightseeing easy by staying in a hotel just a stone's throw away from East Side's main attractions. Millennium Park and Wrigley Field are two visitor favourites.
What are the top hotels in East Side?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are among the most popular properties in East Side. Why not take a look at the amenities and facilities at each and then decide?
How far in advance should I book my East Side holiday?
Your safest bet is to book early. Air carriers usually release flights nearly 12 months ahead of departure, and this is a perfect opportunity to pick up some of the cheapest prices. Boss just told you to take all your holiday days next week? Don't fret. Expedia are never short of fantastic deals to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia East Side travel package include?
Much of that depends on you. You can select from a range of East Side packages, such as a rental car, hotel and flight. You can also book a flight and a hotel, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your ideal East Side trip looks like, you're sure to save!
What should I know before booking an East Side travel package?
You'll land great savings when you combine your hotels, flights and rental cars into a travel package. Not only that, booking everything in one spot makes trip planning much easier. So why waste time or money? Whether you're putting together a fancy romantic getaway or an affordable family break, have a look at our package deals today.
Can I choose my airline with an East Side Expedia travel package?
Most definitely. We have access to over 550 partner airlines around the world, so you can customize your East Side getaway according to your travel needs.

Popular places to visit

Wrigley Field

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier
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

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.

Michigan Avenue

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

£30
per adult
94% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago

* 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.