Southwest Side Holidays from £1,249

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Top Southwest Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,753, price is now £1,249 per person
£1,249
per person
3 Jun - 9 Jun
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The property looks beautiful and the staff is very friendly. The details are, however, very lacking. The window in my room was drafty and upon inspection there were stains on the curtains. The shower had basically no edge to it and the curtain was short enough that the floor flooded when we showered. The bed was also not comfortable- especially the pillows which had zero support. It's a good location but I definitely won't be staying here again.

Reviewed on 19 Mar 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,319, price is now £1,411 per person
£1,411
per person
3 Jun - 9 Jun
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The staff were extremely solicitous! The room was spotless! And the breakfast was delicious, plentiful, and included in the prove of the stay. I’ll definitely be back!

Reviewed on 19 Mar 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £2,053, price is now £1,432 per person
£1,432
per person
3 Jun - 9 Jun
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
There was no kitchen.

Reviewed on 18 Mar 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,674, price is now £1,865 per person
£1,865
per person
3 Jun - 9 Jun
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.

Reviewed on 16 Mar 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,040, price is now £1,452 per person
£1,452
per person
3 Jun - 9 Jun
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The staff was super helpful and very welcoming. The room had an amazing view for us, beings it was our first time being in Chicago. It’s was so close to everything we wanted to visit and super convenient. I will most definitely stay at this hotel again for future stays in the city.!! Thank you so much for taking pride in your establishment, and your employees, as both we’re definitely deserving of a 5 star rating and review.!

Reviewed on 17 Mar 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

Southwest Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

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 £96 per night from 1 Apr to 2 Apr
£96
1 Apr - 2 Apr
includes taxes & fees
8/10 Very Good! (9,967 reviews)
Great room! Love the drawers and closet space! The only down side would be the tv not being able to connect through casting. However, TV channels weren’t all bad.

Reviewed on 19 Mar 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £138 per night from 6 Apr to 7 Apr
£138
6 Apr - 7 Apr
includes taxes & fees
9.4/10 Exceptional! (3,568 reviews)
The staff were extremely solicitous! The room was spotless! And the breakfast was delicious, plentiful, and included in the prove of the stay. I’ll definitely be back!

Reviewed on 19 Mar 2026

Hotel Riu Plaza 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 £115 per night from 29 Mar to 30 Mar
£115
29 Mar - 30 Mar
includes taxes & fees
8.6/10 Excellent! (5,747 reviews)
The hitel is a bit outdated. Overall it was clean. Beds were nit comfortable at all. Not enough elevators to keep up with the very busy hotel needs. We spent more time waiting on the elevators then anything else. The breakfast was average. I am highly disappointed in the fact that the hotel charges ...

Reviewed on 19 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,140 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.
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Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home 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(125 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

£19
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£33
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
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. Flight-inclusive packages are ATOL protected.