Downtown Chicago Holidays

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Your Downtown Chicago Holiday

Reserving a Downtown Chicago holiday package is a great way to get to know this unique neighbourhood. From its must-visit places to its lesser-known delights, you'll be sure to uncover something new. Some leading nearby attractions to see during your trip to Downtown Chicago include Millennium Park, Willis Tower and Art Institute of Chicago. Whatever your travel plans or the size of your budget, booking your dream Downtown Chicago holiday is a cinch with Expedia.

Price found within the past 48 hours. Click for updated prices.
  • Meeting facility
    Jul 28 - Aug 4

    Thompson Chicago, by Hyatt + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.2/10 - Wonderful (1,370 reviews)
    "Excellent hotel and close to restaurants and shopping. Very clean."
    Reviewed May 24, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$4,948
    AU$3,786
    per traveller
    found 1 day ago
    Thompson Chicago, by Hyatt
  • Indoor wedding
    Jul 28 - Aug 4

    Swissotel - Chicago + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.0/10 - Wonderful (3,354 reviews)
    "It was a nice room. Only complaint would be air conditioning. I don’t do hot. Hate sweating. Had turned to 65 and still not really cold. Otherwise overall nice."
    Reviewed May 26, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    Save 100% on your flight
    AU$6,123
    AU$3,882
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Terrace/patio
    Jul 28 - Aug 4

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.4/10 - Exceptional (2,516 reviews)
    "Clean and have a beautiful view of the lake"
    Reviewed May 26, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$5,762
    AU$4,025
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 2 restaurants; breakfast, lunch, and dinner served
    Jul 28 - Aug 4

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.4/10 - Exceptional (3,713 reviews)
    "Gorgeous property in the middle of everything! Staff is so nice and helpful and the rooftop bar can’t be beat!"
    Reviewed May 26, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$6,045
    AU$4,257
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Executive lounge
    Jul 28 - Aug 4

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    8.8/10 - Excellent (2,156 reviews)
    "Amazing view and clean room"
    Reviewed May 25, 2026
    Return • Sydney (SYD) - Chicago (ORD)
    SYD - ORD • 1 stop ORD - SYD • 1 stop
    AU$5,126
    AU$3,886
    per traveller
    found 1 day ago
    Fairmont Chicago at Millennium Park

Our guide on where to stay in Downtown Chicago

Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago
Magnificent Mile

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

Find hotels in Magnificent Mile

Our pick of the best Downtown Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is AU$337 per night from 2 June to 3 June
AU$337
2 June - 3 June
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 26 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is AU$436 per night from 16 June to 17 June
AU$436
16 June - 17 June
includes taxes & fees
9.4/10 Exceptional! (4,257 reviews)
"Great location, great breakfast that's free to guests, great lobby bar. No access to a microwave to heat dinner leftovers. No room service."

Reviewed on 26 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is AU$315 per night from 16 June to 17 June
AU$315
16 June - 17 June
includes taxes & fees
7.8/10 Good! (1,478 reviews)
"El staff es un poco malhumorado Cuando tienes preguntas, la mayoria. Los tickets de comida o drinks gratis en realidad son descuentos, tienes q pagar. Excepto por el desayuno, solo use una vez cada uno, no me agrado, sali afuera. Regrese todos los demas tickets al hacer checkout. Gracias"

Reviewed on 26 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 1,636 properties in Downtown Chicago
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Downtown Chicago holiday package cost?
Go from looking to booking with our Downtown Chicago holiday packages, which start from just . Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure.
How do I get a cheap travel package to Downtown Chicago?
Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1 000 000 hotels across the world, your Downtown Chicago holiday package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It's an easy way to unlock even more savings. The holiday you've always dreamed of in Downtown Chicago is much closer than you thought!
How far in advance should I book my Downtown Chicago holiday?
While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you'll score some incredible deals. If you've left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure.
What does an Expedia Downtown Chicago travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you've made your booking. You're in charge! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Downtown Chicago travel package?
Our prices are always low. However, you'll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.
Can I choose my airline with a Downtown Chicago Expedia holiday package?
Yes — that's the beauty of an Expedia holiday package. You're in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip.
If I'm not able to travel, can I cancel my Downtown Chicago holiday package?
You can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Downtown Chicago holiday package. You may be able to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Downtown Chicago

Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Chicago Riverwalk

Chicago Riverwalk

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

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

AU$55
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago

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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.