Plan a trip to see Oak Street

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The Royal Sonesta Chicago River North

Downtown Chicago

AU$2,576

per person

17 Oct - 24 Oct

found 22 hours ago

Return flight included

Sydney (SYD) to Chicago (ORD)

9.2/10 Wonderful! (2,052 reviews)

We really enjoyed our stay. The staff was super friendly!

Reviewed on 1 Sep. 2025

The Emily Hotel

Downtown Chicago

Save 100% on your flight

AU$3,369

per person

17 Oct - 24 Oct

found 22 hours ago

Return flight included

Sydney (SYD) to Chicago (ORD)

9.2/10 Wonderful! (1,192 reviews)

We have stayed at The Emily Hotel twice and has become our go to for our yearly trip for an event in town. Every time we visit the staff goes above and beyond to ensure a great experience from check in, valet parking, amenities, and room service.

Reviewed on 2 Sep. 2025

Level Chicago – Old Town

Downtown Chicago

AU$2,920

per person

17 Oct - 24 Oct

found 22 hours ago

Return flight included

Sydney (SYD) to Chicago (ORD)

9/10 Wonderful! (343 reviews)

It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug. 2025

Tours & day trips

See all 170 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 36 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 31 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

900 North Michigan Shops

You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Fourth Presbyterian Church

Fourth Presbyterian Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

John Hancock Center

4.5/5(36 reviews)

You can find out about the history of Chicago when you stop by John Hancock Center. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Washington Square

Learn about the local history of Chicago with a stop at Washington Square. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

Oak Street Beach

Why not spend a care-free afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.

Chicago Water Tower

4.5/5(18 reviews)

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.