Near South Side Holidays from £1,329

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Your Near South Side Holiday

Book a holiday package to Near South Side and get set to immerse yourself in its history, walking and culture. However you want to spend your time in this lakeside neighbourhood, there are plenty of opportunities for relaxation and fun. Your trip to Near South Side wouldn't be complete without stopping by leading attractions nearby such as Millennium Park, Willis Tower and Art Institute of Chicago. Don't just dream it — turn it into reality! Secure your ideal Near South Side holiday with Expedia and enjoy travelling your way.

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The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,687, price is now £1,329 per person
£1,329
per person
31 Jul - 3 Aug
found 20 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,325 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

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £2,471, price is now £1,696 per person
£1,696
per person
23 Aug - 29 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.

Reviewed on 14 Jun 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,517, price is now £1,885 per person
£1,885
per person
23 Jul - 30 Jul
found 1 day ago
Return direct flight included
Edinburgh (EDI) 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 £2,169, price is now £1,658 per person
£1,658
per person
23 Jul - 30 Jul
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
The hotel was wonderful. Everything was extremely clean, the entire staff was very friendly, and the service was exceptional. We had the best experience

Reviewed on 14 Jun 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,931, price is now £1,487 per person
£1,487
per person
23 Jul - 30 Jul
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
The front foyer had beautiful glass bulbs that were very dusty and dirty. Not a good first impression Housekeeping or room service could have been disclosed for 4 nights garbage build up Also notice we had no bathroom hooks to hang wet towels just one towel bar. Bed was comfortable and linens were fine. Oh and, $8 bottle of Voss water in room no cups in room or bathroom. Microwave breakfast 😑

Reviewed on 15 Jun 2026

Where to stay in Near South Side

Find the best Near South Side areas and neighborhoods for the activities you enjoy most. Learn more about Near South Side
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Near South Side

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is £207 per night from 1 Jul to 2 Jul
£207
1 Jul - 2 Jul
includes taxes & fees
9.2/10 Wonderful! (1,139 reviews)
"Rooms were clean and modern. Friendly staff. Only problem we had was about the location-quite far from places we wanted to see. Not the hotels fault but just not the right location for our visit."

Reviewed on 16 Jun 2026

Hyatt Regency McCormick Place Chicago
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! (10,292 reviews)
"I understand that this is a historic property built in 1893 and it definitely has that charm, but the upkeep and amenities were surprisingly lacking. My curtains didn't close in my room, the paint in stairwells was peeling off the walls and the shower head and shower curtain hooks were cheap plastic. ..."

Reviewed on 16 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 refundableReserve now, pay when you stay
The price is £142 per night from 21 Jun to 22 Jun
£142
21 Jun - 22 Jun
includes taxes & fees
7.8/10 Good! (1,594 reviews)
"Clean room staff nice"

Reviewed on 15 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,574 properties in Near South 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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Frequently asked questions

How much does a Near South Side travel package cost?
Explore the best of Near South Side from just £1,329. Choose from a wonderful selection of flights, hotels and rental cars to suit every budget. You can score even more discounts when you add a few activities or tours to your travel package.
If I'm not able to travel, can I cancel my Near South Side travel package?
We totally understand — life can throw you the odd curveball. If you've booked a Near South Side travel package and need to amend or cancel it, we're here to help. It's always worth taking a look at our Customer Service Portal first for information. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change your itinerary for free. If it's been more than 24 hours, your airline, hotel or car rental company may charge a fee.
How do I get a cheap travel package to Near South Side?
Combine your hotel and flight bookings, add on extras such as activities or a rental car, and save with a Near South Side travel package. You won't just enjoy wonderful discounts on your adventure — you'll have a world of choice at your fingertips too. When you book with Expedia, you can choose from more than 550 airlines and 1,000,000 hotels throughout the world. Your unforgettable holiday begins right here, right now!
Does Expedia offer Book Now, Pay Later Near South Side holidays?
Yes, we do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply click on the payment plan that works for you during the checkout process and take the stress out of budgeting for your next trip. Make sure you bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's monthly instalment plans. If paying bite-sized amounts each month works for you, pick this option during the checkout process.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan with Klarna.

Where should I stay in Near South Side?
Urban adventurers come from all over the world to see Millennium Park and Wrigley Field in Near South Side. Book yourself a room close to these terrific attractions to make sightseeing a breeze.
What are the top hotels in Near South Side?
If it's your first visit to Near South Side, reserve a room at Hyatt Regency Chicago or The Godfrey Hotel Chicago. Both offer friendly service and are top options with many savvy travellers.
How far in advance should I book my Near South Side holiday?
Travellers are generally able to look up international fares on Expedia up to a year in advance of departure. Booking late? With a stroke of luck, it's still possible to purchase a cheaper ticket only weeks before your journey.
What does an Expedia Near South Side travel package include?
Travel packages include hotels, flights and rental cars, but you can combine any of them to create your dream Near South Side holiday. You can also add on experiences and activities once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll score discounts you won't find anywhere else.
What should I know before booking a Near South Side travel package?
You'll land great savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything in one spot simply makes planning easier. So why waste money or time? Whether you're putting together a ritzy romantic getaway or a low-cost family break, take a look at our package deals today.
Can I choose my airline with a Near South Side Expedia travel package?
Yes — that's the beauty of an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 airline partners across the globe, so you have lots of choice when putting together your Near South Side trip.

Stay near popular Near South Side attractions

Photo by © City of Chicago
Open Photo by © City of Chicago

Soldier Field

8.8/5 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
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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.