Plan a trip to see Roosevelt University

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Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

per person

17 Oct - 24 Oct

found 15 hours ago

Return direct flight included

Sydney (SYD) to Chicago (ORD)

9.4/10 Exceptional! (2,063 reviews)

Everything was beautiful close to dining and shopping the beds were comfortable it was so relaxing looking out the window unto the ocean. Don’t hesitate book now

Reviewed on 11 Aug. 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

17 Oct - 24 Oct

found 15 hours ago

Return direct flight included

Sydney (SYD) to Chicago (ORD)

9.4/10 Exceptional! (1,679 reviews)

Terrace 16 resto has the best view in Chicago outstanding service. Hotel is located right next to the river cruises. Walgreens is 3 minutes away by foot. Very safe neighborhood several excellent restaurants within 10 minutes on foot. Try Wildberry resta for breakfast excellent food. Sanda for Asian food and Grand Boucher French The pizza place next to hotel (bonjiourno) overrated and subpar

Reviewed on 12 Aug. 2025

The Langham, Chicago

Downtown Chicago

per person

17 Oct - 24 Oct

found 15 hours ago

Return direct flight included

Sydney (SYD) to Chicago (ORD)

9.8/10 Exceptional! (1,004 reviews)

Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug. 2025

Tours & day trips

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Architecture River Tour

Free cancellation available

Food, drink & nightlife

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Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

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Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

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Chicago White Sox Baseball Game at Guaranteed Rate Field

Popular places to visit

Auditorium Building and Theatre

You can make plans for a show at Auditorium Building and Theatre on your trip to Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

Printer\'s Row showing heritage architecture and a city

Harold Washington Library Center

Harold Washington Library Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Discover the fascinating museums and notable monuments in this vibrant area.

Art Institute of Chicago

From ancient masterpieces to eclectic modern art, uncover a treasure trove of works from all over the world and throughout history.

Lollapalooza

After visiting Lollapalooza, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Jazz Institute of Chicago

You can enjoy some culture when you stop by Jazz Institute of Chicago in Chicago. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.