The Loop 2026 Holidays & City Breaks | Flight + Hotel

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

Eurostars Magnificent Mile

Downtown Chicago

€659

per person

6 Sept - 11 Sept

found 1 day ago

Return flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

9/10 Wonderful! (3,732 reviews)

There was no early check-in unfortunately. All staff were very friendly and helpful. Really grateful for the sturdy umbrellas in the room.

Reviewed on 3 Aug 2026

Level Chicago – Old Town

Downtown Chicago

€907

per person

6 Sept - 11 Sept

found 1 day ago

Return flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

9/10 Wonderful! (509 reviews)

Hotel Felix River North/Magnificent Mile

Downtown Chicago

€807

per person

24 Sept - 29 Sept

found 1 day ago

Return flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

8.2/10 Very good! (2,858 reviews)

Room was clean & hotel staff was very friendly!

Reviewed on 3 Aug 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

€1,262

per person

9 Oct - 12 Oct

found 11 hours ago

Return flight included

New York (JFK) to Chicago (ORD)

9.4/10 Exceptional! (2,606 reviews)

Overall I had a very good stay over there. My one complaint was there wasn't a microwave in the room.

Reviewed on 3 Aug 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

€1,115

per person

16 Oct - 19 Oct

found 11 hours ago

Return flight included

New York (JFK) to Chicago (ORD)

9.6/10 Exceptional! (1,945 reviews)

could have better menu in their restaurants

Reviewed on 3 Aug 2026

Where to stay in The Loop

Find the best The Loop areas and neighborhoods for the activities you enjoy most. Learn more about The Loop

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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.

Top hotels in The Loop

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

€162

30 Aug - 31 Aug

includes taxes & fees

8/10 Very good! (10,192 reviews)

"The only good thing about this Hotel is that it’s next to downtown Chicago, besides that I would never use that hotel again"

Reviewed on 4 Aug 2026

The Allegro Royal Sonesta Hotel Chicago Loop

171 W Randolph St Chicago IL

Fully refundableReserve now, pay when you stay

€264

30 Aug - 31 Aug

includes taxes & fees

9/10 Wonderful! (2,722 reviews)

"It was our first time touring in Chicago. We are from San Francisco. Loved this hotel! The lobby is beautiful. It has a great restaurant and bar. The staff is very friendly and accommodating. Would definitely stay here again."

Reviewed on 3 Aug 2026

Fairmont Chicago at Millennium Park

200 North Columbus Drive Chicago IL

Fully refundableReserve now, pay when you stay

€350

15 Aug - 16 Aug

includes taxes & fees

8.8/10 Excellent! (2,293 reviews)

"The staff was excellent in every area we encountered (front desk, The Lounge, housekeeping, room service, and the amazing gentlemen out front)"

Reviewed on 3 Aug 2026

See all 1,214 properties in The Loop

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.

Frequently asked questions

How much does a The Loop holiday package cost?

Much less than you might think — from as low as €659, in fact! By bundling flights, hotels and car rentals into your own custom-made package, your The Loop escape is only clicks away.

How do I get a cheap travel package to The Loop?

Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you cash too. A The Loop holiday package makes it easy to organise the perfect trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your schedule will be no sweat. Not only that, we have over 1,000,000 properties globally to select from. Now that's what you call choice. Whatever your budget, Expedia will help show you the world.

Where should I stay in The Loop?

A journey to The Loop isn't over until you've seen McCormick Place and Millennium Park. Look for somewhere to stay within walking distance so you can easily access these impressive tourist attractions.

What are the top hotels in The Loop?

If it's your first time staying in The Loop, make a reservation at Canopy by Hilton Chicago Central Loop or Hilton Garden Inn Chicago Central Loop. Both hotels offer comfy beds and are favourites with many travellers.

How far in advance should I book my The Loop holiday?

To bag rock-bottom prices, book nice and early. Airlines typically advertise flights, along with some of the lowest fares, nearly a year prior to departure. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you were hoping for a last-minute getaway to The Loop, there are always plenty of great deals on Expedia. Check them out now!

What does an Expedia The Loop travel package include?

That depends on what you want. If you're travelling solo, you might decide to bundle flights and hotels. Taking the whole family to The Loop? A travel package including flights, hotels and rental cars might suit you better. Expedia gives you the freedom to customize your travel package.

Can I choose my airline with a The Loop Expedia holiday package?

Most definitely. Expedia has over 550 partner airlines to choose from globally. With so many choices, finding the ideal carrier to whisk you away to The Loop will be a snap.

If I'm not able to travel, can I cancel my The Loop holiday package?

We totally understand that life sometimes gets in the way of your plans. If you've booked a The Loop holiday package and need to cancel or change it, we're here to help. We recommend browsing 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 and rebook for free. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.

Stay near popular The Loop attractions

A river with boats, surrounded by tall buildings and a clear sky.

Chicago Riverwalk

9.6/10 (13,574 reviews)

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

See properties