Old Town Chicago Vacations from $281

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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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
Save 100% on your flight
$281
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,015 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$411
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
The hotel is very centrally located! We got a room with a view and so worth it. Get the lake view you won’t be disappointed! Will definitely stay there again!

Reviewed on Oct 11, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$393
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
$480
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
$976
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (532 reviews)

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
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
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotels in Magnificent Mile
A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

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A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Find hotels in Lincoln Park

Old Town Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
$126 total
Nov 11 - Nov 12
Total with taxes and fees
Congress Plaza Hotel
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
$181 total
Oct 25 - Oct 26
Total with taxes and fees
8.8/10 Excellent! (5,521 reviews)
"Great hotel"

Reviewed on Oct 11, 2026

River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$143 nightly
$170 total
Nov 1 - Nov 2
Total with taxes and fees
8/10 Very Good! (2,471 reviews)
"Hotel was unique and enjoyed the location. Room was very basic but functional. Lobby was very welcoming."

Reviewed on Oct 11, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,535 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.
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Stay near popular Old Town Chicago attractions

Second City

9.6/10 (15 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.
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Lighthouse ArtSpace Chicago

You can spend time studying the exhibits at Lighthouse ArtSpace Chicago during your trip to Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.
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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.
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Midwest Buddhist Temple

After visiting Midwest Buddhist Temple, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or visit the shops in this vibrant area.
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House of Glunz

8.4/10 (6 reviews)
You can search for that perfect souvenir at House of Glunz during your visit to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
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Hudson Chess Park

Explore the great outdoors at Hudson Chess Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$158
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
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.