
East Side Vacation Packages
Book a Stay + Flight or Car to save on your trip
East Side Vacation Packages
East Side Vacation Packages
Now's the time to plan your dream East Side escape. Sit back and let the hardworking staff at Orbitz bundle up top-value hotel and flight combos for you. Imagine all the things you could buy with savings of up to $374. Just pick your desired airfares, hotels, experiences and rental cars to save cash! On top of that, our comprehensive database has no less than 500,000 hotels across the world and 500 partner airlines. Don't stress if you have trouble selecting — we'll make it easy! Our packages will help you design that adventure you've been dreaming about. With limitless possible options to combine your flights and hotels, the only thing you have to do is pack your bags!
Where is East Side?
East Side — you've heard plenty about it, you're itching to get there but don't have an inkling where it is? Let us point you in the right direction. It's a neighborhood in the much-loved city of Chicago. You'll find it located 13 miles south of the downtown area. There are 2,700,000 locals that live in Chicago.Places to Visit in East Side
Crisp air and beautiful surroundings are found in abundance at Calumet Park. But wait, there are still more options! Whether you want to rule the baccarat table, try your luck at a game of poker or just soak up the high-stakes atmosphere, Horseshoe Hammond Casino offers a fun-filled night out.
Car Rentals in East Side
Pump up the volume on your favorite driving tunes and discover East Side from the freedom of your own ride. You'll find some of the biggest and best car rentals in East Side on Orbitz. Arriving via Midway International Airport? Once you're off the tarmac, you can pick up a vehicle within minutes. Budget and Avis are both a short distance from baggage claim. Renting a car in East Side means venturing out to one of the surrounding areas. Journey to Washington Heights, home to Enterprise at 1820 W 87Th St.
Places to Visit in East Side
Crisp air and beautiful surroundings are found in abundance at Calumet Park. But wait, there are still more options! Whether you want to rule the baccarat table, try your luck at a game of poker or just soak up the high-stakes atmosphere, Horseshoe Hammond Casino offers a fun-filled night out.
Nearest Airports to East Side
It can be disconcerting arriving in a foreign place, but the more you know about your destination, the easier it'll be. The closest airport to East Side is Midway International Airport (MDW). It sits 12 miles to the northwest of the neighborhood.
Popular Places to Visit Near East Side
Irondale and Merrionette Manor are well worth visiting while you are in East Side. Irondale is about 1 mile away, while Merrionette Manor is 2 miles away.
No Cancellation Fees
Life taken an unexpected turn recently? Do you need to alter your booking? Don't stress — we won't expect you to pay a fee.^ Be mindful that your airline and hotel might charge you one though, so get on to them quickly!
Top East Side vacation package deals

Four Points by Sheraton Chicago O'Hare Airport
Jun 10 - Jun 17
Atlanta (ATL) to Chicago (ORD)
Reviewed on Dec 15, 2024

Congress Plaza Hotel
Jun 10 - Jun 17
Atlanta (ATL) to Chicago (ORD)
Reviewed on Apr 28, 2025


Hilton Chicago/Magnificent Mile Suites
Jun 10 - Jun 17
Atlanta (ATL) to Chicago (ORD)
Reviewed on Apr 24, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
Jun 10 - Jun 17
Atlanta (ATL) to Chicago (ORD)
Reviewed on May 2, 2025
Top rated hotels for your East Side vacation package

Congress Plaza Hotel

Hilton Chicago/Magnificent Mile Suites
