Old Town Chicago Vacations from $576

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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.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$576
per person
Sep 26 - Sep 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
$865
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
$859
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
I am regular at this hotel and always satisfied with my stay

Reviewed on Aug 21, 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
Save 100% on your flight
$1,013
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,335 reviews)
Lovely place in Westloop, close to everything, quiet, clean and efficient. I would stay there again.

Reviewed on Aug 20, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$727
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 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 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 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 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.

Find hotels in River North
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.

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Old Town Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$109 nightly
$130 total
Sep 8 - Sep 9
Total with taxes and fees
8/10 Very Good! (10,271 reviews)
"Room 406: Clean and quiet."

Reviewed on Aug 20, 2026

Congress Plaza 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
Aug 30 - Aug 31
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$250 nightly
$294 total
Sep 11 - Sep 12
Total with taxes and fees
Hilton Chicago O'Hare Airport
See all 4,484 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 entertainment choices.
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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.
See properties

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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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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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 lively bars.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.