
Downtown Chicago Vacation Packages
Book a Stay + Flight or Car to save on your trip
Downtown Chicago Vacation Packages
Downtown Chicago Vacation Packages
Kick back, relax and let the specialist team at Orbitz help you craft an amazing Downtown Chicago getaway. If you're looking to combine your flight and hotel options to save some money, you're in the right place! It's easy to save by packaging your bookings. Select your preferred airfares, hotels, rental cars and experiences and you can save up to $374! And remember — you've got heaps of versatility. Mix and match from 500 airlines and more than 500,000 worldwide hotels. There are limitless available options to suit you and your unique style. All you need to do is decide on your package deal and prepare for a spectacular getaway.
Where is Downtown Chicago?
A happy, stress-free vacation starts with doing your homework. Read on to learn just where Downtown Chicago is. It's a neighborhood in the fantastic city of Chicago. You'll find it located 0.6 miles northeast of the downtown area. Forget the big attractions — it's the locals that make a place tick. Here in Chicago, you'll discover 2,700,000 of them.Car Rentals in Downtown Chicago
Your getaway starts with car rentals in Downtown Chicago. Whether you’d love to jump off the tourist trail or just like the convenience of having your own wheels, Orbitz will help you find the keys to your ride. Collecting a vehicle right at Midway International Airport means that you don't have to deal with transfers and cabs. You won't have to go far to find Budget and Avis. Sometimes the easiest place to rent a ride is right in the city center. Hertz is a handy outlet situated at 151 E Wacker Dr. You can also try Enterprise at 10 E Grand Hilton Garage.
Where to stay in Downtown Chicago – Hotel Accommodation
Lock in your hotel in Downtown Chicago ASAP and begin organizing the remainder of your thrilling getaway. Orbitz presently has 165 available options in this place. Do you want a room that'll make you feel like a king? Our top high-end hotels are the Waldorf Astoria Chicago and The Peninsula Chicago. Otherwise, the Old Chicago Inn (3222 N Sheffield Ave) and the Urban Holiday Lofts (2014 W Wabansia) are suitable options if you're visiting on a budget. You'll be pleased to hear that there are several hotel options within strolling distance of the Art Institute of Chicago if you fancy staying close by. The Langham, Chicago is just 0.6 miles away. If that doesn't suit, check yourself into the JW Marriott Chicago, which is 0.5 miles away.
Nearest Airports to Downtown Chicago
Located 9 miles southwest of Downtown Chicago, Midway International Airport (MDW) is where your getaway begins. Once you've gotten your suitcase from the baggage area, you'll be discovering the sights and sounds of Chicago before you know it!
Popular Places to Visit Near Downtown Chicago
Take the chance to check out some nearby destinations such as Near East Side or Michigan Avenue. Near East Side is about 0.2 miles from Downtown Chicago, while Michigan Avenue is 0.2 miles away.
No Cancellation Fees
Need to cancel or amend your booking? Nervous about a big fee? You'll be delighted to hear that we don't have one!^ Fingers crossed, your chosen hotel and airline don't either, but it would be wise to check in with them regarding their rules.
Top Downtown Chicago vacation package deals

Hilton Grand Vacations Club Chicago Magnificent Mile
Jan 29 - Feb 1
Boston (BOS) to Chicago (ORD)
Reviewed on Aug 31, 2024

The Westin Michigan Avenue Chicago
Dec 10 - Dec 12
Boston (BOS) to Chicago (ORD)
Chicago (ORD) to Boston (BOS)
Reviewed on Oct 18, 2025

Pendry Chicago
Jan 29 - Feb 1
Boston (BOS) to Chicago (ORD)
Reviewed on Jul 5, 2024

Level Chicago – Old Town
Jan 5 - Jan 9
Boston (BOS) to Chicago (ORD)
Chicago (ORD) to Boston (BOS)
Reviewed on Feb 16, 2024

Trump International Hotel & Tower Chicago
Jan 29 - Feb 1
Boston (BOS) to Chicago (ORD)
Reviewed on Oct 13, 2025
Top rated hotels for your Downtown Chicago vacation package

Embassy Suites by Hilton Chicago Downtown River North

Congress Plaza Hotel

Hilton Chicago/Magnificent Mile Suites
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