Essex Vacations from $733
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Your Essex Vacation
When a break in the city is calling, answer it with a vacation package to Essex. The neighborhood of Magnificent Mile, which is great for cafes, shopping and history, makes an excellent base for your adventures. Every trip to Essex needs a well-planned itinerary. Fill yours with leading attractions like University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field. No matter your travel plans or budget, organizing a tailored Essex vacation is a walk in the park with Expedia.
The Latest Essex Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,081, price is now $733 per person
$733
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Perfect location and staff was great!
Reviewed on Jun 27, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,190, price is now $778 per person
$778
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,284, price is now $867 per person
$867
per person
Aug 8 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,217, price is now $824 per person
$824
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
Views were amazing on the water with a bonus fireworks show. Thanks Sable!
Reviewed on Jun 26, 2026
Where to stay in Essex
Find the best Essex areas and neighborhoods for the activities you enjoy most. Learn more about Essex
Downtown Chicago
5 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.
Essex Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,133 reviews)
"The hotel is a bit run down, but my room was very clean. The breakfast was good, although it is not included, and for some reason I thought it was. The receptionist was amazing. She was very kind and allowed me to check in early, which I really appreciated. The location is also excellent. I’m giving ..."
Reviewed on Jun 26, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $175 total per night from Jul 5 to Jul 6
$175 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (4,464 reviews)
"Location was great. Everything at the hotel from checkin to chef out was very smooth."
Reviewed on Jun 26, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $231 total per night from Jul 5 to Jul 6
$231 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (4,547 reviews)
"No hot water in shower and toilet didn’t flush properly."
Reviewed on Jun 27, 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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
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.