Far Southwest Side Holidays

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Top Flight + Hotel Deals in Far Southwest Side

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 €2,026, price is now €1,429 per person
€1,429
per person
23 May - 30 May
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
I found the price you pay for breakfast inclusion there would be more options then a danish, fruit, yogurt, and a coffee that there is a limitation on how much you get. The room was clean, there was issues with plumbing but they were working on fixing it. On the second floor the walls are thin I could hear every word of the TV in the next room. The TV also lost signal multiple times and it would take forever for the tv to come back on.

Reviewed on 18 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €2,588, price is now €1,670 per person
€1,670
per person
23 May - 30 May
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Yessss it’s was amazing

Reviewed on 13 Apr 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 €2,598, price is now €1,766 per person
€1,766
per person
23 May - 30 May
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Hard to find the parking . Everything at navy pier closes at 8pm . Staff offered no extras even though it says we are vip Expedia and hiltons honors .

Reviewed on 17 Apr 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was €2,402, price is now €1,677 per person
€1,677
per person
23 May - 30 May
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.

Reviewed on 14 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was €3,369, price is now €2,373 per person
€2,373
per person
23 May - 30 May
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
Celebrate my birthday here and upon arrival was given champagne. It made my evening even better. I felt at home will be returning

Reviewed on 18 Apr 2026

Where to stay in Far Southwest Side

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

Beverly is well liked for its restaurants and churches. If you're hoping to see more of the larger area, Chicago State University and Jones Convocation Center are some interesting sights nearby to check out.

Find hotels in Beverly

Top hotels in Far Southwest Side

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 €140 per night from 10 May to 11 May
€140
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (4,152 reviews)
When I looked around the hotels near this one were several times more expensive…ie, The Four Seasons is very close by. While we know that’s a huge upgrade, the Hilton was clean, friendly and in a great location. We came back to sleep! The rooms are dated, but ours separated the king sized “bedroom” ...

Reviewed on 18 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
Fully refundableReserve now, pay when you stay
The price is €155 per night from 26 Apr to 27 Apr
€155
26 Apr - 27 Apr
includes taxes & fees
8.6/10 Excellent! (5,859 reviews)
Clean and easy check in.

Reviewed on 17 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
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! (10,137 reviews)
We were in room 500, great corner room! I love the old charm. Traffic noise is a bit much and it was a Thursday evening. I imagine a holiday weekend in that area would be pretty noisy. But the bed was comfy! Staff is very courteous. I would stay again, I'll try for floor 12 next time.

Reviewed on 18 Apr 2026

Congress Plaza Hotel
See all 4,843 properties in Far 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 Far Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€38
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
94% of travellers recommend
Art Institute of Chicago
See all activities in Far Southwest Side

Frequently asked questions

Can I cancel my flight booking to Far Southwest Side due to COVID-19?
If you've yet to book your tickets, check the terms and conditions of the airfare you're considering. If you've already reserved your flight to Far Southwest Side, make use of our Customer Service Portal. It will help determine which COVID-19 policies are applicable to your reservation and provide you with the next steps.
What's the best way to find cheap flights to Far Southwest Side that have flexible change policies?
When it comes to travelling these days, flexibility is crucial. That's why we've added a "No change fee" filter to help you locate cheap and flexible tickets to Far Southwest Side. It's near the top left of your screen directly under the "Flexible change policies" heading.
What are some of the general tips for travellers to Far Southwest Side during the COVID-19 outbreak?
COVID-19 has ushered in dramatic changes to how we travel. If you're planning an escape to Far Southwest Side, these tips will help you navigate these new rules and challenges:
  • Before you lock in a flight, check if any travel restrictions apply — in both your origin and destination. Stay informed with the latest updates by reviewing government travel advisories.
  • When you go through airport screening, keep your face mask on. You will be required to lower it briefly to verify your identity. Passengers who refuse to wear a mask may be fined and denied boarding.
  • Rather than handing a TSA agent your boarding pass, position it directly on the reader yourself. After that, hold it up for inspection.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on bags. This will have to be removed from your bag for scanning.
  • Place any personal items (e.g, keys, phone and wallet) in your carry-on rather than a bin to reduce handling during the screening process.
  • Separate any food you have for X-ray screening. Putting it in a clear plastic bag and into a bin reduces the need for a TSA employee to handle and inspect your belongings.

Which airlines fly to Far Southwest Side?
Organise your seat with American Airlines and then start putting together your Far Southwest Side travel itinerary. This leading carrier provides 13307 flights every month to O'Hare Intl. Airport (ORD), a main gateway.
How can I find cheap tickets to Far Southwest Side?
In the last seven days, was the lowest price for a flight to Far Southwest Side. For an even cheaper fare, book well ahead of time and be flexible with your dates. Search for your trip to Far Southwest Side, then compare prices for nearby days by clicking on the "flexible dates" link above.
How much is a flight to Far Southwest Side?
In the last seven days, round-trip airfares to Far Southwest Side sold from just and reached a maximum price of . For one-way fares taking off from (), the cheapest seat during this time was only .
What are the most popular airports to fly into in Far Southwest Side?
Start arranging your Far Southwest Side holiday by booking a fare on one of the 33491 flights each month to O'Hare Intl. Airport (ORD). This is the region's main entry point.
When is the cheapest time to fly to Far Southwest Side?
If you'd prefer to spend your holiday money enjoying the best of Far Southwest Side rather than on your flight there, jet off earlier in the week. The most affordable day to travel is normally Tuesday, with Monday a close second. With many folks travelling over the weekend, Saturday often has the highest ticket prices.
How much is a plane ticket to Far Southwest Side?
Fares to Far Southwest Side varied from to in the last seven days. Typically, the quicker you book the better the price.
Which airlines with flights to Far Southwest Side employ COVID-19 cleanliness policies?
As countries begin to open their borders, most airlines have resumed business with new measures including physical distancing and enhanced disinfection measures. Here's what different carriers are doing to ease the spread of COVID-19:
  • 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.