Old Town Chicago Vacations from $295

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Your Old Town Chicago Vacation

Experience the best that Old Town Chicago has to offer with a tailor-made Old Town Chicago vacation package. From its cafes and bars and pubs to its history, you'll quickly fall for the charms of this commercial neighborhood. When it's time to see the sights, you'll find lots of big-name attractions nearby including Wrigley Field, Millennium Park and Willis Tower. Tick off one, two or all during your trip to Old Town Chicago. Expedia will help turn your ideal Old Town Chicago vacation into reality, no matter your travel plans or budget.

The Latest Old Town Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites, Lincolnshire by IHG

Staybridge Suites, Lincolnshire by IHG

3 out of 5
Half Day
Save 100% on your flight
per person
Oct 22 - Oct 27
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
In a great neighborhood. Quiet, clean. Excellent room layout. Free laundry was very nice to have. Nice breakfast.

Reviewed on Aug 14, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Nov 7 - Nov 12
found 11 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (431 reviews)
This is my go to place in the south suburbs.

Reviewed on Jul 30, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,631 reviews)
The rooms were beautiful and very well updated. The hotel is only a 20 minute walk from Navy Pier with plenty of great dining options around. The Red Line station is steps from the front door which made everything very accessible.

Reviewed on Aug 18, 2025

Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
Save 100% on your flight
per person
Oct 22 - Oct 27
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
8/10 Very Good! (1,008 reviews)
The room i stayed in had 4 different blue lights from the TV, M/C, red lighta from phone and clock and a flashing blue motion detector type light which madw it hard to fall asleep.

Reviewed on Aug 18, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
The rooftop should be guest only or have a better security as some people skip to other floors with no cards and be a security threat

Reviewed on Aug 18, 2025

Where to stay in Old Town Chicago

Find the best Old Town Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Chicago
Downtown Chicago showing a city

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.

Find hotels in Downtown Chicago

Old Town Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$157 nightly
The price is $184 total per night from Sep 1 to Sep 2
$184 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (8,965 reviews)
"Its location is the main reason why I chose to stay. The room has been updated; it is roomy and clean. Staffs are very friendly and helpful."

Reviewed on Aug 17, 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $177 total per night from Sep 1 to Sep 2
$177 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (1,194 reviews)
"Staff was kind and friendly."

Reviewed on Aug 17, 2025

The Wade
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
$161 nightly
The price is $189 total per night from Sep 3 to Sep 4
$189 total
Sep 3 - Sep 4
Total includes taxes and fees
8.4/10 Very Good! (4,717 reviews)
"Kids really enjoyed the pool. Breakfast was good as well"

Reviewed on Aug 17, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,599 properties in Old Town Chicago
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

Discover the most popular places to visit in Old Town Chicago

Second City

4.5/5(10 reviews)

You can enjoy a show at Second City during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Second City

Lighthouse ArtSpace Chicago

You can spend time studying the exhibits at Lighthouse ArtSpace Chicago during your trip to Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

Lighthouse ArtSpace Chicago

Henry Gerber House

Learn about the local history of Chicago with a stop at Henry Gerber House. Stroll along the lakeside or visit the shops in this vibrant area.

Henry Gerber House

Things to do

River tour boat in Chicago

Architecture River Tour

$41
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.