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Featured Old Town Chicago 4 Star hotels

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Mar 23 to Mar 24
CA $167
CA $196 total
Mar 23 - Mar 24
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,721 reviews)
It was awesome

Reviewed on Mar 6, 2026

Opens in a new windowEmbassy Suites by Hilton Chicago Downtown River North
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Mar 22 to Mar 23
CA $148
CA $174 total
Mar 22 - Mar 23
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,711 reviews)
Location and staff

Reviewed on Mar 6, 2026

Opens in a new windowThe Wade
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Mar 24 to Mar 25
CA $179
CA $248 total
Mar 24 - Mar 25
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (3,468 reviews)
It was a wonderful and relaxing stay.. Especially the breakfast I was very impressed 😀

Reviewed on Mar 6, 2026

Opens in a new windowHotel Riu Plaza Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $266 per night from Mar 28 to Mar 29
CA $266
CA $312 total
Mar 28 - Mar 29
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,225 reviews)
Yed

Reviewed on Mar 4, 2026

Opens in a new windowHilton Chicago O'Hare Airport
Pendry Chicago

Pendry Chicago

4.5 out of 5
230 North Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $273 per night from Mar 22 to Mar 23
CA $273
CA $377 total
Mar 22 - Mar 23
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (1,138 reviews)
Front desk staff are gems! They knew my name after 1 interaction and were very attentive. The room amenities were very nice-- espresso, bottled water, chocolates, steamer, toiletries.

Reviewed on Mar 1, 2026

Opens in a new windowPendry Chicago
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Apr 6 to Apr 7
CA $185
CA $210 total
Apr 6 - Apr 7
includes taxes & fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,392 reviews)
B da

Reviewed on Mar 7, 2026

Opens in a new windowHyatt Regency O'Hare Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Apr 1 to Apr 2
CA $177
CA $247 total
Apr 1 - Apr 2
includes taxes & fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,663 reviews)
The room was very good with great view of Lake Michigan.

Reviewed on Mar 7, 2026

Opens in a new windowHilton Chicago
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from Mar 23 to Mar 24
CA $195
CA $229 total
Mar 23 - Mar 24
includes taxes & fees
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (3,304 reviews)
Great location, kind staff, clean room. Shower head was a little odd but they have a hand held mode as well which worked better. Would visit again!

Reviewed on Mar 7, 2026

Opens in a new windowEurostars Magnificent Mile
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Apr 5 to Apr 6
CA $208
CA $291 total
Apr 5 - Apr 6
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (3,472 reviews)
More options for breakfast would be nice

Reviewed on Mar 6, 2026

Opens in a new windowHyatt Regency Chicago
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $310 per night from Mar 21 to Mar 22
CA $310
CA $364 total
Mar 21 - Mar 22
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (3,628 reviews)
.

Reviewed on Mar 6, 2026

Opens in a new windowLondonHouse Chicago, Curio Collection by Hilton
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