West Side Vacation Packages 2026 from $308

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The Latest West Side vacation packages

Price found within the past 48 hours. Click for updated prices.

Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Save 100% on your flight

$308

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7.6/10 Good! (2,711 reviews)

Very dated property. A bit rundown and not all that clean. Very good location however.

Reviewed on Aug 17, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$570

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Overall, this is a great hotel. My family loved the rooms and the fitness center. The staff were mostly great too. We will definitely stay here again if we come back to Chicago. We were given rooms that were 28 floors apart despite making our reservation months in advance. Yes, it was one reservation which included 2 rooms. Both the shower and toilet space was fairly tight. Other than that, we are very happy.

Reviewed on Aug 18, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$677

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

N/a

Reviewed on Aug 18, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$695

per person

Nov 2 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (1,960 reviews)

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$385

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (2,899 reviews)

Great location and pleasant staff.

Reviewed on Aug 17, 2026

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Where to stay in West Side

Find the best West Side areas and neighborhoods for the activities you enjoy most. Learn more about West Side

A cityscape with modern skyscrapers and a curved highway.

West Loop

1 out of top 10 points of interest in this area

Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.

A train at a station with a cityscape in the background.

West Town

2 out of top 10 points of interest in this area

Noted for its live music and theaters, there's plenty to explore in West Town. Top attractions like The Salt Shed and Milwaukee Avenue are major draws, and you can hop on the metro at Division Station or Damen Station to see more of the city.

A city skyline with modern skyscrapers, a parking lot, and a distinctive building with a geometric facade.

Near West Side

4 out of top 10 points of interest in this area

Live music, theaters, and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Polk Station (Pink Line) or Racine Station to get around town.

A train crossing an elevated bridge over a city street with buildings and greenery.

Wicker Park

Consider exploring the abundant dining options in Wicker Park. If sightseeing is on the list, Milwaukee Avenue is a top attraction. Hop on the metro at Damen Station or Division Station to see more of the area.

A cityscape with a prominent skyscraper, dense urban buildings, and a green park area.

Lower West Side

The bars and museums are just a few things visitors like about Lower West Side. National Museum of Mexican Art and The Geraghty are worthwhile spots to check out, and you can hop on the metro at Damen Station (Pink Line) or 18th Station (Pink Line) to get around the larger area.

Stay near popular West Side attractions

A large, modern building with a curved facade and multiple vertical windows.

United Center

8.8/10 (4,269 reviews)

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

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A cityscape with a prominent skyscraper, a circular building, and a large rectangular building.

University of Illinois Chicago

8.4/10 (1,058 reviews)

Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.

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A riverside path with a stone edge, lush greenery, and yellow flowers.

Humboldt Park

7.0/10 (2 reviews)

Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed theater scene and fascinating museums in this vibrant area.

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A greenhouse with diverse tropical plants and a large glass structure.

Garfield Park Conservatory

9.0/10 (6 reviews)

While away the afternoon in this huge conservatory housing tropical and rare plants, waterfalls and art.

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Credit Union 1 Arena

8.0/10 (5 reviews)

Catch an event at Credit Union 1 Arena during your trip to Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.

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The Salt Shed

You can get tickets for a performance at The Salt Shed during your stay in Chicago. Experience the live music and theater scene in this vibrant area.

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Anna and Frederick Douglass Park

7.0/10 (12 reviews)

After visiting Anna and Frederick Douglass Park, make a plan to see the other sights and activities in Chicago. Experience the fascinating museums and acclaimed art scene in this vibrant area.

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Union Park

After visiting Union Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

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What to do in West Side

360 CHICAGO Observation Deck

$27

per adult

86% of travellers recommend

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47

per adult

88% of travellers recommend

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25

per adult

90% of travellers recommend

See all activities in West Side

West Side Hotel Deals

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street Chicago IL

Fully refundableReserve now, pay when you stay

$173 nightly

$205 total

Aug 30 - Aug 31

Total with taxes and fees

9/10 Wonderful! (2,523 reviews)

"The staff was very helpful! They were able to hold our bags after checkout since we had later flights."

Reviewed on Aug 18, 2026

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street Chicago IL

$167 nightly

$199 total

Sep 8 - Sep 9

Total with taxes and fees

8.6/10 Excellent! (1,165 reviews)

"WiFi was a little bit temperamental other than that it was a great experience."

Reviewed on Aug 16, 2026

The Emily Hotel

311 North Morgan Street Chicago IL

Fully refundableReserve now, pay when you stay

$289 nightly

$344 total

Aug 30 - Aug 31

Total with taxes and fees

9.2/10 Wonderful! (1,339 reviews)

"No closet, no drawers. Rooms were small. No pool. Coffee maker not plugged in. Lots of wasted space after poorly planned renovations. Difficulty in getting ready to go out due to small vanity area. Tight fit in room for more than two people. Good location and friendly staff"

Reviewed on Aug 18, 2026

See all 805 properties in West 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.