Best Flight From Luis Munoz Marin Intl. To CHI

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Amazing SJU to CHI Flight Deals

The cheapest flights to CHI-All Airports were $155 for round trip flights and $44 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, May 24 - Fri, May 29
SJU
San Juan
ORD
Chicago
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 24 from San Juan to Chicago, returning Fri, May 29, priced at $155 found 1 day ago
Sun, May 24 - Fri, May 29
SJU
San Juan
ORD
Chicago
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 24 from San Juan to Chicago, returning Fri, May 29, priced at $176 found 1 day ago
Fri, May 15 - Mon, May 18
SJU
San Juan
ORD
Chicago
$186 Roundtrip, found 20 hours ago
$186
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Fri, May 15 from San Juan to Chicago, returning Mon, May 18, priced at $186 found 20 hours ago
Fri, May 1 - Mon, May 4
SJU
San Juan
ORD
Chicago
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, May 1 from San Juan to Chicago, returning Mon, May 4, priced at $187 found 1 day ago
Thu, Apr 30 - Mon, May 11
SJU
San Juan
ORD
Chicago
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Apr 30 from San Juan to Chicago, returning Mon, May 11, priced at $189 found 1 day ago
Thu, May 14 - Mon, May 18
SJU
San Juan
ORD
Chicago
$196 Roundtrip, found 2 days ago
$196
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 14 from San Juan to Chicago, returning Mon, May 18, priced at $196 found 2 days ago

Hotels near CHI-All Airports Airport (CHI)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
$125 nightly
The price is $148 total per night from May 25 to May 26
$148 total
May 25 - May 26
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
8.2/10 Very Good! (2,655 reviews)
It was ok

Reviewed on Apr 28, 2026

Opens in a new windowHotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$126 nightly
The price is $148 total per night from Apr 29 to Apr 30
$148 total
Apr 29 - Apr 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
8.8/10 Excellent! (5,143 reviews)
Everything was great until morning then our room filled up with smoke otherwise it was good

Reviewed on Apr 27, 2026

Opens in a new windowRiver Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
$116 nightly
The price is $138 total per night from May 25 to May 26
$138 total
May 25 - May 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
8.8/10 Excellent! (3,472 reviews)
Quite. Clean, Safe

Reviewed on Apr 27, 2026

Opens in a new windowClub Quarters Hotel, Central Loop, Chicago
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Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$216 nightly
The price is $254 total per night from May 23 to May 24
$254 total
May 23 - May 24
Total with taxes and 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 staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.
8.4/10 Very Good! (2,280 reviews)
If you get stuck at O’Hare Airport overnight then this is the place to stay

Reviewed on Apr 27, 2026

Opens in a new windowHilton Chicago O'Hare Airport
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$150 nightly
The price is $178 total per night from May 25 to May 26
$178 total
May 25 - May 26
Total with taxes and 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 Riverwalk are located nearby.
9.4/10 Exceptional! (3,987 reviews)
Clean sleek room & bathroom! Staff was friendly and courteous! They have a breakfast buffet and I was expecting something simple and walked right into a 5 star breakfast and setup! The view from my room was mid because I was facing other people rooms in another hotel .. however I was on the 26 floor ...

Reviewed on Apr 28, 2026

Opens in a new windowHotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$139 nightly
The price is $165 total per night from May 10 to May 11
$165 total
May 10 - May 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9/10 Wonderful! (4,225 reviews)
Outdated for a hilton seemed old and dingy. Rooms had no proper ac. The lighting was poor. The bathroom was small, the shampoos were emoty poor attention to detail. I would soend my money elsewhere. Location was ok if your shopping. The restaurant was good but it is independently owned.

Reviewed on Apr 28, 2026

Opens in a new windowHilton Chicago/Magnificent Mile Suites
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
$149 nightly
The price is $177 total per night from May 25 to May 26
$177 total
May 25 - May 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
8.8/10 Excellent! (2,292 reviews)
The pool was ice cold.

Reviewed on Apr 27, 2026

Opens in a new windowHoliday Inn Chicago Dwtn - The Mart by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$132 nightly
The price is $157 total per night from May 9 to May 10
$157 total
May 9 - May 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
8/10 Very Good! (10,159 reviews)
The location is ideal - cross the street and you are greeted with a large park which looks well maintained. There are plenty of dining options in the area within walking distance. Rideshare or cabs are plentiful. The staff were terrific. From the front desk to the maid service. All were friendly ...

Reviewed on Apr 28, 2026

Opens in a new windowCongress Plaza Hotel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Picks

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.