The Loop Vacations

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  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Room service - dining
    Jul 15 - Jul 20

    The Wade + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    8.4/10 - Very Good (1,844 reviews)
    "The bathroom door is sliding and does not close completely and the extractor does not work. Excellent location, valet parking somewhat disorganized, staff 3.5/5 of kindness."
    Reviewed May 26, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥455,390
    ￥353,707
    per traveler
    found 7 hours ago
    The Wade
  • Terrace/patio
    Jul 15 - Jul 20

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,887 reviews)
    "Location, cleanliness, overall staff assistance and service and of course breakfast"
    Reviewed May 26, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥548,170
    ￥435,320
    per traveler
    found 7 hours ago
    Trump International Hotel & Tower Chicago
  • Exterior detail
    Jul 30 - Aug 5

    The Emily Hotel + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,324 reviews)
    "One of the worst hotel rooms I have stayed in. Tables and drawers made out of plywood, very uncomfortable beds, tv was mounted on side of bed so you had to turn to side to watch it. Low lights, makeup light mounted on opposite side of plug in so you had a cord in front of the mirror. Super basic and not worth the price. Location, bar and coffee were only positives. Would not stay here again."
    Reviewed May 26, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥565,609
    ￥456,772
    per traveler
    found 18 hours ago
    The Emily Hotel
  • Dinner served
    Jul 15 - Jul 20

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,000 reviews)
    "Great hotel. Loved the lobby and our room. Would definitely stay here again."
    Reviewed May 19, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥444,254
    ￥365,090
    per traveler
    found 7 hours ago
    Kimpton Gray Hotel by IHG
  • Lobby
    Jul 15 - Jul 20

    The Langham, Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,002 reviews)
    "hands down one of the nicest hotels in the city - pool/gym/spa are all amazing. such a good 2nd floor lounge with great views. the staff is all so helpful, friendly"
    Reviewed May 26, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥566,982
    ￥473,233
    per traveler
    found 7 hours ago
    The Langham, Chicago

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
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

The Loop Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is ￥32,286 per night from Jun 2 to Jun 3
￥32,286
￥38,386 total
Jun 2 - Jun 3
includes taxes & fees
8/10 Very Good! (10,144 reviews)
"Our hvac unit in the room was one of the loudest I’ve ever had the displeasure of sleeping near. Had to turn it off to get sleep. Great views but definitely some historic wear that needs new paint in halls, elevator entries, etc. front doors were partially defunct our entire stay. No onsite parking ..."

Reviewed on May 26, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is ￥30,038 per night from May 27 to May 28
￥30,038
￥35,710 total
May 27 - May 28
includes taxes & fees
8.8/10 Excellent! (5,207 reviews)
"Great location clean rooms"

Reviewed on May 26, 2026

River Hotel
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
The price is ￥42,116 per night from May 27 to May 28
￥42,116
￥55,743 total
May 27 - May 28
includes taxes & fees
8.8/10 Excellent! (2,171 reviews)
"Stayed here for a recent trip to Chicago and overall the experience was okay. The location is convenient for downtown attractions and Millennium Park, and the hotel itself was clean and comfortable. Staff were generally polite and check-in was fairly smooth. The rooms were decent, though some areas ..."

Reviewed on May 26, 2026

Fairmont Chicago at Millennium Park
See all 1,220 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 vacation package cost?
Much less than you might think — from as low as , 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 vacation package makes it easy to organize 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 favorites with many travelers.
How far in advance should I book my The Loop vacation?
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 traveling 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 vacation 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 vacation package?
We totally understand that life sometimes gets in the way of your plans. If you've booked a The Loop vacation 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.

Discover the most popular places to visit in The Loop

Millennium Park

Millennium Park

4.5/5(7,309 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Chicago Riverwalk

Chicago Riverwalk

4.5/5(1,558 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.

Chicago Riverwalk
Willis Tower

Willis Tower

4.5/5(3,420 reviews)

Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.

Willis Tower

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,236
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,904
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,276
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.