Name: Congress Plaza Hotel
Price range: $215 total
Rating: 8

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The Latest Southwest Side vacation packages

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

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$788

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (512 reviews)

We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on Jul 2, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$920

per person

Sep 14 - Sep 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (2,809 reviews)

Excellent spot, in the perfect location. Parking at the property is pretty expensive, but there are cheaper parking garages close by.

Reviewed on Jul 6, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

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$919

per person

Sep 14 - Sep 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,586 reviews)

Anderson should receive a gold star! So helpful, patient, and has such a great personality. The room was clean on arrival but I did notice housekeeping never cleaned our room during our stay and we had to ask for fresh hand towels every morning. Breakfast was standard and I would definitely like to see an ice machine or at least the juice in the dispenser be cold. The burgers from the bar were good but the pepperoni pizza was very disappointing especially for $22.

Reviewed on Jul 7, 2026

Four Seasons Hotel Chicago

Downtown Chicago

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$1,602

per person

Sep 14 - Sep 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,006 reviews)

We came to the property for my wife’s 40th birthday celebration. From the moment we walked in through the doors, we felt pampered. Everyone on staff was friendly, high energy, and always willing to help. The housekeeping staff was top notch as they went above and beyond with expectation on not only keeping things clean, but organizing our clutter, leaving thoughtful birthday treats, and making us feel comfortable. I now do not want to travel without staying at a 4 seasons property. They made our experience 10 times better!

Reviewed on Jul 6, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$1,109

per person

Sep 14 - Sep 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,566 reviews)

The hotel was on the pier and

Reviewed on Jul 7, 2026

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Where to stay in Southwest Side

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

Clearing

4/5(72 area reviews)

You'll appreciate the restaurants during your time in Clearing and you might want to plan a stop by Wintrust Sports Complex and SeatGeek Stadium while you're in the area.

Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)

After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

See properties

What to do in Southwest Side

360 CHICAGO Observation Deck

$22

per adult

86% of travellers recommend

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25

per adult

88% of travellers recommend

Flyover in Chicago

$31

per adult

96% of travellers recommend

See all activities in Southwest Side

Southwest Side Hotel Deals

Omni Chicago Hotel

676 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$197 nightly

$234 total

Jul 9 - Jul 10

Total with taxes and fees

9.2/10 Wonderful! (1,874 reviews)

"Convenient location and friendly staff."

Reviewed on Jul 7, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$163 nightly

$193 total

Jul 27 - Jul 28

Total with taxes and fees

8.2/10 Very Good! (1,709 reviews)

"Rooms were spacious and clean. Would stay again."

Reviewed on Jul 8, 2026

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$181 nightly

$215 total

Jul 9 - Jul 10

Total with taxes and fees

8/10 Very Good! (10,200 reviews)

"Dated hotel but the rooms are kept clean, updated flooring and really nice bedding. Fantastic location downtown, less than a mile walking distance from Museum Campus."

Reviewed on Jul 7, 2026

See all 4,820 properties in Southwest 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.