Southwest Side Holidays

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Top Flight + Hotel Deals in Southwest Side

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €1,367, price is now €1,051 per person
€1,051
per person
21 May - 25 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Nice hotel I would stay here again

Reviewed on 15 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,892, price is now €1,374 per person
€1,374
per person
21 May - 25 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Yessss it’s was amazing

Reviewed on 13 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,938, price is now €1,544 per person
€1,544
per person
21 May - 25 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on 7 Apr 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was €1,334, price is now €1,071 per person
€1,071
per person
21 May - 25 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
Rooftop bar is amazing

Reviewed on 14 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was €1,757, price is now €1,415 per person
€1,415
per person
21 May - 25 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,225 reviews)
Great location, service wasn’t the greatest, fees are high, crib was outdated.

Reviewed on 13 Apr 2026

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
artist paints mural on a city street

Back of the Yards

2 out of top 10 points of interest in this area

While there might not be top attractions in Back of the Yards, you can explore the larger area and discover places like Bridgeport Art Center and Zhou B Art Center.

Find hotels in Back of the Yards

Top hotels in Southwest Side

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €115 per night from 26 Apr to 27 Apr
€115
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,147 reviews)
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Reviewed on 14 Apr 2026

Congress Plaza Hotel
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 €136 per night from 26 Apr to 27 Apr
€136
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,123 reviews)
We stayed after seeing Hamilton at CIBC Easter weekend. The hotel was busy, but service was quick and representatives were very friendly. The remodeled pool was great for my 11 year old niece.

Reviewed on 15 Apr 2026

Hilton Chicago/Magnificent Mile Suites
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
The price is €156 per night from 10 May to 11 May
€156
10 May - 11 May
includes taxes & fees
8.6/10 Excellent! (5,839 reviews)
Breakfast was great compared to other hotels. The ac worked so that was good. The tv kept cutting off but i think it was because we were streaming so i wasnt too upset. Great staff!

Reviewed on 15 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,130 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.

Popular places to visit

Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

5/5(1 review)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier

What to do in Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
94% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€35
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Southwest Side

Frequently asked questions

Can I cancel my flight booking to Southwest Side due to COVID-19?
Our handy Customer Service Portal is where you can get important information about cancelling your Southwest Side flight due to COVID-19. Before you reserve a seat, it's smart to look over the terms and conditions of your airfare too.
What's the best way to find cheap flights to Southwest Side that have flexible change policies?
We know that plans can change in the blink of an eye, so booking a flexible airfare with Expedia is always a wise idea. Tick the "No change fee" box below the "Flexible change policies" filter. Your affordable, flexible flight to Southwest Side is only a few clicks away.
What are some of the general tips for travellers to Southwest Side during the COVID-19 outbreak?
In the face of COVID-19, travelling now comes with a few extra challenges. Keep in mind these worthwhile tips before boarding your plane to Southwest Side:
  • Understand what rules and restrictions apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so remember to check before you book your flight.
  • When you go through airport checkpoints, keep your face mask on. You will be asked to briefly lower it for identification purposes. Travellers who refuse to wear a face mask may face civil penalties and may also be denied boarding.
  • Instead of handing a TSA officer your boarding pass, place it directly on the reader yourself. When that's done, hold it up for inspection.
  • One container of liquid hand sanitizer is now permitted in your carry-on baggage. It must be no bigger than 12 oz (350 ml), and you'll have to take it out of your bag at the X-ray machine for screening.
  • Put any personal items (phone, wallet and keys for example) in your carry-on rather than a bin to minimize handling during the screening process.
  • If you want to take food on board, put it in a clear plastic bag and then into a screening bin. This reduces the likelihood that a TSA officer will need to touch your carry-on bag or food container for inspection.

Which airlines fly to Southwest Side?
American Airlines operates flights into or near Southwest Side, including 13307 that touch down at O'Hare Intl. Airport (ORD) each month. Work out your holiday dates and then lock in your ticket early for the biggest bargain.
How can I find cheap tickets to Southwest Side?
You'll always walk away with a fabulous deal with Expedia, but our "flexible dates" search function makes it that much easier. Enter your preferred flight date, then click on the flexible dates link above to see a list of prices for nearby days. was the best price for a flight to Southwest Side in the last seven days.
How much is a flight to Southwest Side?
There were plenty of low-cost fares up for grabs in the last seven days, with the cost of a return ticket to Southwest Side varying between and . Many lucky holiday makers purchased one-way seats from () for just .
What are the most popular airports to fly into in Southwest Side?
The main entryway to Southwest Side, roughly 33491 flights service O'Hare Intl. Airport (ORD) each month. Look for a top deal, reserve your fare and get set to soak up the best of this renowned region.
When is the cheapest time to fly to Southwest Side?
If you're not set on what day you jet off to Southwest Side, try to fly out earlier in the week. The cheapest day to take off is normally Tuesday, closely followed by Monday. Saturday is typically the priciest day, with lots of holiday makers choosing to fly on the weekend.
How much is a plane ticket to Southwest Side?
In the last seven days, flights to Southwest Side varied between and . Prices generally depend on the departure time, airline, cabin class and when the fare is booked.
Which airlines with flights to Southwest Side employ COVID-19 cleanliness policies?
As people begin travelling again, most commercial airlines have implemented physical distancing and other vital actions to reduce the impact of COVID-19. These carriers are among them:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.