Plan a trip to see Stephen A. Douglas Tomb and Memorial

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Pendry Chicago

Downtown Chicago

AU$1,421

per person

26 Sept - 28 Sept

found 1 day ago

Return direct flight included

Orlando (MCO) to Chicago (ORD)

9.4/10 Exceptional! (1,059 reviews)

Will be coming back! Beautiful rooms and great staff.

Reviewed on 24 Aug. 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

AU$1,566

per person

26 Sept - 28 Sept

found 1 day ago

Return direct flight included

Orlando (MCO) to Chicago (ORD)

9.4/10 Exceptional! (1,690 reviews)

This property is beautiful and located in a great area.

Reviewed on 19 Aug. 2025

The Emily Hotel

Downtown Chicago

AU$1,498

per person

26 Sept - 28 Sept

found 1 day ago

Return direct flight included

Orlando (MCO) to Chicago (ORD)

9.2/10 Wonderful! (1,182 reviews)

The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug. 2025

Tours & day trips

See all 174 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 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 14 activities

Chicago White Sox Baseball Game at Guaranteed Rate Field

Popular places to visit

Illinois Institute of Technology

Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

McCormick Tribune Center

You can find out about the history of Chicago with a visit to McCormick Tribune Center. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Zhou B Art Center

You can spend time browsing the exhibits at Zhou B Art Center during your trip to Chicago. Experience the acclaimed art galleries and entertainment choices in this vibrant area.

Bridgeport Art Center

You can spend time browsing the exhibits at Bridgeport Art Center during your travels in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Bubbly Creek

Commune with nature and explore the great outdoors at Bubbly Creek during your travels in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Theatre on the Lake

You can make plans for a show at Theatre on the Lake on your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.