Southwest Side Holidays from £1,570

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Top Southwest Side Flight + Hotel Deals

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

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £2,097, price is now £1,570 per person
£1,570
per person
31 Jul - 5 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
The staff was great. The room was nice but I would have preferred more towels. The remote in our room wasn’t working fully as well as the steamer in the room. Otherwise, it is a good hotel but would not recommend for families.

Reviewed on 15 Jun 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,340, price is now £1,772 per person
£1,772
per person
31 Jul - 5 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,735 reviews)
Excellent hotel to stay in. Surrounded by so many things Chicago has to offer. Right across from the river. We were greeted nicely, was able to upgrade to a nicer room at a fair price. Check in was smooth. Room was very nice, well maintained hotel lobby, rooms hallways etc. had breakfast in the Land and Sea restaurant downstairs due to a rainy morning. Would definitely recommend staying at the London House for a stay in Chicago.

Reviewed on 15 Jun 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,143, price is now £1,647 per person
£1,647
per person
31 Jul - 5 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Great location and food court in area. Great for family fun

Reviewed on 17 Jun 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,581, price is now £2,012 per person
£2,012
per person
31 Jul - 5 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,888 reviews)
Very clean rooms, helpful staff and great amenities! Close to everything and convenient to shopping and eating Felt safe and comfortable in the area !

Reviewed on 15 Jun 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £2,473, price is now £1,948 per person
£1,948
per person
31 Jul - 5 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The hotel is beautiful with so many bars and restaurants nearby. About 4 -5 blocks from Millenium Park. The seating areas are so peaceful and the design is amazing. They let me store my bike box the day before my stay which was so convenient. Staff are friendly and professional.

Reviewed on 17 Jun 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
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Clearing

Visitors to Clearing appreciate its restaurants. A visit to Wintrust Sports Complex and SeatGeek Stadium might round out your trip if you're looking to see more of the area.

Find hotels in Clearing

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 £121 per night from 29 Jun to 30 Jun
£121
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,295 reviews)
"Have to pay for parking plus the ac barely works"

Reviewed on 17 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is £141 per night from 1 Jul to 2 Jul
£141
1 Jul - 2 Jul
includes taxes & fees
7.8/10 Good! (1,588 reviews)
"Amazing! My daughter and I loved it, including the location."

Reviewed on 17 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £123 per night from 2 Jul to 3 Jul
£123
2 Jul - 3 Jul
includes taxes & fees
8.8/10 Excellent! (2,687 reviews)
"Hotel main trash service pickup was directly below my room window and was extremely loud when unloading and loading rolloff dumpsters at 4am. No way to sleep through the noise. Shuttle service was very good to and from the airport. Toilet clogged after one use with no plunger available. Remodeling ..."

Reviewed on 17 Jun 2026

Hyatt Regency O'Hare Chicago
See all 4,978 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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Stay near popular Southwest Side attractions

Marquette Park

9.4/5 (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 galleries.
See properties

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.