Downtown Chicago Vacations from $233

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Your Downtown Chicago Vacation

Reserving a Downtown Chicago vacation package is a great way to get to know this unique neighborhood. From its must-visit places to its lesser-known delights, you'll be sure to uncover something new. Some leading nearby attractions to see during your trip to Downtown Chicago include Millennium Park, Willis Tower and Art Institute of Chicago. Whatever your travel plans or the size of your budget, booking your dream Downtown Chicago vacation is a cinch with Expedia.

The Latest Downtown Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham South Holland

Super 8 by Wyndham South Holland

2 out of 5
per person
Jun 20 - Jun 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.6/10 Good! (1,012 reviews)
Overall the hotel was neat and clean. The staff was pleasant.

Reviewed on Apr 15, 2025

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90

2 out of 5
Woodlawn
per person
Jun 26 - Jul 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
3/10 (6 reviews)
Pay little and get little. That’s the deal. Staff was courteous and helpful.

Reviewed on Mar 2, 2025

Red Carpet Inn Great Lakes

Red Carpet Inn Great Lakes

2 out of 5
per person
Jun 26 - Jul 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
5.8/10 (1,000 reviews)
Nice and clean. Service and personal are very good. The best one in this price range. Thank you.

Reviewed on Apr 14, 2025

Howard Johnson by Wyndham Merrillville

Howard Johnson by Wyndham Merrillville

2.5 out of 5
per person
Jun 3 - Jun 9
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
6.6/10 (1,001 reviews)
Carpeting in hallways was soiled and frayed, tv not working in the room. First room was extremely smoky, so requested a different room which was somewhat better. Dresser drawers were broken in the second room.

Reviewed on Apr 7, 2025

Chicago Getaway Hostel

Chicago Getaway Hostel

2 out of 5
Lincoln Park
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (1,013 reviews)
Nice spot but bad parking

Reviewed on Apr 23, 2025

Where to stay in Downtown Chicago

Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago
Magnificent Mile - River North

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

Downtown Chicago Hotel Deals

Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $241 per night from May 11 to May 12
$241
includes taxes & fees
$205 per night
May 11 - May 12
8.8/10 Excellent! (2,074 reviews)
"Clean rooms, great location, next to everything in the city."

Reviewed on Apr 23, 2025

Swissotel - Chicago
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
Fully refundableReserve now, pay when you stay
The price is $169 per night from May 1 to May 2
$169
includes taxes & fees
$144 per night
May 1 - May 2
8.2/10 Very Good! (3,927 reviews)
"Overall we enjoyed the stay and the property location is close to many restaurants, shops and subway. The complimentary breakfast was great."

Reviewed on Apr 23, 2025

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $189 per night from Apr 30 to May 1
$189
includes taxes & fees
$161 per night
Apr 30 - May 1
8.8/10 Excellent! (2,147 reviews)
"Great stay. The only thing is that it said there would be a city view and the view was of the building roofs. Also the pool was closed. The room was lovely and spacious."

Reviewed on Apr 23, 2025

Hilton Chicago/Magnificent Mile Suites
See all 1,569 properties in Downtown 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 Downtown Chicago

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Grant Park showing a garden and night scenes

Grant Park

4.5/5(3,318 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Things to do

Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

$49
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

$45
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Chicago

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