East Side Holidays from £655

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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.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£655
per person
7 Jan - 12 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
Save 100% on your flight
£830
per person
7 Jan - 14 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,015 reviews)
The staff was 10/10.

Reviewed on 15 Oct 2026

Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
£1,521
per person
22 Dec - 28 Dec
found 1 hour ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,003 reviews)
Excellent experience. I’d recommend this property for their outstanding service and updated rooms.

Reviewed on 9 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,327
per person
19 Nov - 23 Nov
found 5 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Clean space to relax and enjoy your trip

Reviewed on 15 Oct 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£946
per person
22 Dec - 28 Dec
found 1 hour ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)

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
A busy city street with tall buildings, a bus, and cars.

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
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

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
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.

Find hotels in The Loop
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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
A wooden pavilion with a view of a city skyline and a body of water.

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.

Find hotels in Lincoln Park

Top hotels in East Side

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£95
11 Nov - 12 Nov
includes taxes & fees
8/10 Very good! (10,130 reviews)
"The door staff weee excellent! They were helpful with all of my questions."

Reviewed on 16 Oct 2026

Congress Plaza Hotel
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£136
1 Nov - 2 Nov
includes taxes & fees
River Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
£115
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,406 reviews)
"Great stay.."

Reviewed on 16 Oct 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,201 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
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Holiday in Month
Where to go when
Where to go when

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 £655. 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.

Stay near popular East Side attractions

Calumet Park

8.0/10 (1 review)
Explore the great outdoors at Calumet Park, a lovely green space in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
See properties

Munson Beach

Why not spend a lazy afternoon at Munson Beach during your trip to Chicago? While you're in the area, wander around the parks.
See properties

Calumet Beach

Why not spend a lazy afternoon at Calumet Beach during your trip to Chicago? While you're in the area, wander around the parks.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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.