What's it like in Uptown?

Uptown is a neighbourhood that travellers like for its theatres, live music and lake views. Looking for sights you might find in a travel guide about Uptown? Consider a visit to Lake Michigan while you're in the neighbourhood.

Where is the best place to stay in Uptown?

Based on Expedia customer reviews, The Guesthouse Hotel is the highest ranked property in Uptown. This hotel offers private balconies and a fitness centre.

How many hotels will I be able to find in the Uptown area?

If you're searching for places to stay in Chicago, Expedia has something to meet your needs with 38 Uptown hotels and other accommodation options to choose from.

If I need to cancel my hotel reservation in Uptown, will I receive a refund?

Yes! Most hotel bookings are fully refundable provided that you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and be given a refund within 24 hours of booking. Add dates, click "Search", then you can use the "fully refundable" filter to get the top deals on offer in Uptown.

What are the top things to see and do in Uptown?

Spend some time exploring the great outdoors at Lake Michigan, Lincoln Park and Challenger Park. Aragon Ballroom and Riviera Theatre are some other stops worth a visit in the neighbourhood. Wrigley Field, Pegasus Players and Aragon Entertainment Center are just a few of the places to visit in and around Uptown. While you're out sightseeing in Chicago, make sure that you visit other sights such as About Face Theater or Hutchinson Street Historic District.

How can I get around Uptown and the greater Chicago area?

If you want to see more of the city, Wilson Station is the closest metro stop. Others nearby include Lawrence Station and Argyle Station. If you want to head out of town, you can hop aboard a train at Chicago Ravenswood Station.

Top 10 Uptown Hotels of 2026 | Expedia Singapore

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Our top choices for Uptown hotels

The Guesthouse Hotel

Uptown

Loren

includes taxes & fees

22 Feb - 23 Feb

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 9.3 km from Uptown

Blake

includes taxes & fees

22 Feb - 23 Feb

The Wade

Streeterville, 8.6 km from Uptown

Danielle

includes taxes & fees

22 Mar - 23 Mar

The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 7 km from Uptown

Sheila

includes taxes & fees

22 Feb - 23 Feb

Hotel Riu Plaza Chicago

Streeterville, 8.4 km from Uptown

Brisa

includes taxes & fees

4 Mar - 5 Mar

Palmer House a Hilton Hotel

Theatre District, 9.7 km from Uptown

Melani

includes taxes & fees

6 Mar - 7 Mar

Swissotel - Chicago

9.2 km from Uptown

Jon

includes taxes & fees

22 Feb - 23 Feb

Congress Plaza Hotel

The Loop, 10.4 km from Uptown

Jennifer

includes taxes & fees

13 Mar - 14 Mar

Hilton Garden Inn Chicago Downtown South Loop

The Loop, 11 km from Uptown

Quayshaun

includes taxes & fees

1 Mar - 2 Mar

Aloft Chicago Mag Mile

Streeterville, 8.5 km from Uptown

Pablo

includes taxes & fees

5 Mar - 6 Mar

The Blackstone, Autograph Collection

The Loop, 10.6 km from Uptown

Yu Ching Dexter

includes taxes & fees

22 Feb - 23 Feb

Silversmith Hotel Chicago Downtown

Theatre District, 9.6 km from Uptown

Corey

Hyatt Centric The Loop Chicago

Theatre District, 9.6 km from Uptown

Stephanie

includes taxes & fees

27 Feb - 28 Feb

Pendry Chicago

Theatre District, 9.1 km from Uptown

Marcelo

includes taxes & fees

15 Mar - 16 Mar

Staypineapple, An Iconic Hotel, The Loop

Theatre District, 9.4 km from Uptown

Lori

includes taxes & fees

6 Mar - 7 Mar

Hilton Chicago

The Loop, 10.7 km from Uptown

Andrea

includes taxes & fees

22 Mar - 23 Mar

Arlo Chicago

Theatre District, 9.3 km from Uptown

Jennifer

includes taxes & fees

1 Mar - 2 Mar

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Theatre District, 9.7 km from Uptown

Kaiya

includes taxes & fees

8 Mar - 9 Mar

Fairmont Chicago at Millennium Park

The Loop, 9.3 km from Uptown

Kamilah

includes taxes & fees

21 Feb - 22 Feb

2 restaurants, breakfast, lunch, dinner served; American cuisine

LondonHouse Chicago, Curio Collection by Hilton

The Loop, 9 km from Uptown

Osama

includes taxes & fees

22 Feb - 23 Feb

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Where to stay in Uptown

Find the best Uptown areas for the activities you enjoy most.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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Magnificent Mile

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

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The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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O'Hare

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.

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