East Side Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to €900 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 easyPlan, book, and manage your trip all in one place
The Latest East Side Holiday Packages
- Eurostars Magnificent Mile
24 Sept - 29 SeptEurostars Magnificent Mile + Flight
Downtown Chicago5 nights4.0 star property9.0/10 - Wonderful (3,776 reviews)"There was no early check-in unfortunately. All staff were very friendly and helpful. Really grateful for the sturdy umbrellas in the room."Reviewed August 3, 2026Return • New York (EWR) - Chicago (ORD)EWR - ORD • Direct ORD - EWR • 1 stop€1,105€762found 1 day agoper traveller - Level Chicago – Old Town
6 Sept - 11 SeptLevel Chicago – Old Town + Flight
Downtown Chicago5 nights4.0 star property9.0/10 - Wonderful (512 reviews)Return • New York (EWR) - Chicago (ORD)EWR - ORD • Direct ORD - EWR • Direct€1,452€878found 14 hours agoper traveller - Sable at Navy Pier Chicago, Curio Collection by Hilton
20 Sept - 25 SeptSable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago5 nights4.0 star property9.4/10 - Exceptional (2,640 reviews)"Everything was great."Reviewed August 4, 2026Return • New York (EWR) - Chicago (ORD)EWR - ORD • Direct ORD - EWR • Direct€1,605€996found 1 hour agoper traveller - Hotel Felix River North/Magnificent Mile
24 Sept - 29 SeptHotel Felix River North/Magnificent Mile + Flight
Downtown Chicago5 nights4.0 star property8.2/10 - Very good (2,898 reviews)"The hotel location is great, walking distance to many amenities and restaurants. The staff was friendly and welcoming. Although the room was quite small with the basics the bed and pillows were very comfortable."Reviewed August 4, 2026Return • New York (EWR) - Chicago (ORD)EWR - ORD • Direct ORD - EWR • 1 stop€1,291€808found 1 day agoper traveller - Trump International Hotel & Tower Chicago
16 Oct - 19 OctTrump International Hotel & Tower Chicago + Flight
Downtown Chicago3 nights5.0 star property9.6/10 - Exceptional (1,965 reviews)"could have better menu in their restaurants"Reviewed August 3, 2026Return • New York (JFK) - Chicago (ORD)JFK - ORD • Direct ORD - JFK • Direct€1,531€1,116found 23 hours agoper traveller
Discover the most popular places to visit in East Side
East Side Hotel Deals
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton"Everything was great."
"Used latex gloves left on bed and floor. Stained sheets. The shower made a noisy. Only outlet that worked was in the bathroom."
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop
"The only good thing about this Hotel is that it’s next to downtown Chicago, besides that I would never use that hotel again"
Best Western Grant Park Hotel
Best Western Grant Park Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel"The location to the museum campus (walking distance) and L station (a couple blocks) made this location a great base. The room was clean and the bed was very comfortable. Staff was friendly and helpful."
Frequently Asked Questions
How much does an East Side holiday package cost?
Our East Side holiday packages, which start from just €762, are an awesome way to save precious money. Select your preferred hotels, flights and more to create your ideal escape.
How do I get a cheap travel package to East Side?
Bundle your hotels and flights with Expedia to save on your next adventure. With more than 550 air carriers and 1,000,000 properties globally, your East Side holiday package can be customized exactly to suit your budget. With all that extra money, why not throw in one or two interesting tours and experiences? It's an easy way to unlock even more bargains. That dream holiday to East Side is closer than you thought!
Where should I stay in East Side?
With popular attractions such as Calumet Beach and Calumet Park in this area, look for a hotel positioned near either one. Bronzeville Childrens Museum is another East Side sight that lures the crowds.
How far in advance should I book my East Side holiday?
Reserving your spot early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to 12 months in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, low prices to East Side sometimes emerge just weeks before departure.
What does an Expedia East Side travel package include?
Car rentals, hotels and flights — we connect you to the very best deals. All you'll have to do is pick and choose your preferred combination. After you've made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to customize an amazing East Side escape.
What should I know before booking an East Side travel package?
We already have low prices. However, you'll pick up even better deals if you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and tons of choice.
Can I choose my airline with an East Side Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our holiday packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my East Side holiday package?
Don't stress if you're rethinking your East Side holiday package — you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We realise life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.