Near East Side Vacations from $666

Book a Hotel + Flight or Car together to unlock savings

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Your Near East Side Vacation

Lock in a vacation package to Near East Side and get set to experience its nature, walking and views. However you're planning to spend your getaway in this lakeside neighborhood, there's no shortage of opportunities for both relaxation and adventure. Can't wait to sightsee during your trip to Near East Side? Make sure you check out nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago. No matter your travel plans or budget, booking a perfect Near East Side vacation has never been easier with Expedia.

The Latest Near East Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,039, price is now $666 per person
$666
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,037 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,649, price is now $942 per person
$942
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (523 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,231, price is now $758 per person
$758
per person
Sep 25 - Sep 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (501 reviews)
Good

Reviewed on Jul 20, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,294, price is now $830 per person
$830
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,035 reviews)
One of the best places we’ve ever stayed. We had an amazing view of downtown Chicago from our floor, and our executive suite was clean and comfortable. We thoroughly enjoyed our stay and would definitely come back. The customer service and our room were excellent.

Reviewed on Jul 20, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,563, price is now $1,014 per person
$1,014
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)

Where to stay in Near East Side

Find the best Near East Side areas and neighborhoods for the activities you enjoy most. Learn more about Near East Side
A busy city street with tall buildings, a bus, and cars.

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.

Find hotels in Downtown Chicago

Near East Side Hotel Deals

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$245 nightly
The price is $291 total per night from Aug 9 to Aug 10
$291 total
Aug 9 - Aug 10
Total with taxes and fees
9/10 Wonderful! (3,502 reviews)
"The deposit is $1000, which they don’t tell you until check in"

Reviewed on Jul 20, 2026

Swissotel - Chicago
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
221 N Columbus Dr Chicago IL
Fully refundableReserve now, pay when you stay
$263 nightly
The price is $312 total per night from Aug 16 to Aug 17
$312 total
Aug 16 - Aug 17
Total with taxes and fees
8.6/10 Excellent! (2,004 reviews)
"Disappointing Stay — Gorgeous Building, Everything Else Falls Short ​Don’t be fooled by the striking, wavy architecture of the landmark Aqua tower. While the building itself is an architectural marvel from the street, the actual guest experience at the Radisson Blu Aqua Hotel leaves a lot to be desired. ..."

Reviewed on Jul 20, 2026

Radisson Blu Aqua Hotel Chicago
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$189 nightly
The price is $215 total per night from Aug 6 to Aug 7
$215 total
Aug 6 - Aug 7
Total with taxes and fees
Hyatt Regency O'Hare Chicago
See all 4,440 properties in Near East Side
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Stay near popular Near East Side attractions

Swissotel Chicago

After visiting Swissotel Chicago, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$22
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.