East Side Holidays from £966
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages 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, 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
Downtown Chicago
£1,157
per person
22 Oct - 26 Oct
found 19 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
The staff was very friendly and the room was always clean and organized. I was a bit nervous what to expect as a solo traveler and it being my first time staying in Chicago but this was the perfect hotel for the trip. It always felt safe on property and very close to all the main things I wanted to see.
Reviewed on 31 Aug 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
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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
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.
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.
Top hotels in East Side
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£92
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,241 reviews)
"Check-in was super quick and staff was very efficient and helpful. Booked a standard room with a king size bed facing the lake and it was a very nice weekend stay. Room was very clean. The AC is off central heatingThe location is incredibly convenient if you’re going somewhere near the lake or ..."
Reviewed on 31 Aug 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£133
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (2,139 reviews)
"Location near the lake and very walkable to train, bus stations, restaurants and stores. Room was not very well cleaned"
Reviewed on 31 Aug 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (883 reviews)
"Unfortunately this property was a bad experience. There is little to no communication from the host. Your only option is to talk to a chat bot from California. We tried checking in 10 minutes early and were told that wasn't possible, There was no one at the check-in desk when we got there. The room ..."
Reviewed on 31 Aug 2026
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.
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 £966. 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.
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.
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.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
* 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.