Best Flight From Bradley Intl. To CHI

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Amazing BDL to CHI Flight Deals

The cheapest flights to CHI-All Airports were $244 for round trip flights and $113 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Aug 13 - Sun, Aug 16
BDL
Hartford
ORD
Chicago
$244 Roundtrip, found 1 day ago
$244
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 13 from Hartford to Chicago, returning Sun, Aug 16, priced at $244 found 1 day ago
Sat, May 16 - Sat, May 23
BDL
Hartford
ORD
Chicago
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, May 16 from Hartford to Chicago, returning Sat, May 23, priced at $257 found 1 day ago
Wed, May 13 - Sat, May 16
BDL
Hartford
ORD
Chicago
$268 Roundtrip, found 5 days ago
$268
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Wed, May 13 from Hartford to Chicago, returning Sat, May 16, priced at $268 found 5 days ago
Thu, Aug 13 - Sun, Aug 16
BDL
Hartford
ORD
Chicago
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 13 from Hartford to Chicago, returning Sun, Aug 16, priced at $297 found 1 day ago
Tue, Jul 28 - Sat, Aug 1
BDL
Hartford
ORD
Chicago
$321 Roundtrip, found 14 hours ago
$321
Roundtrip
found 14 hours ago
Select Bargain Flight flight, departing Tue, Jul 28 from Hartford to Chicago, returning Sat, Aug 1, priced at $321 found 14 hours ago
Thu, Nov 5 - Mon, Nov 9
BDL
Hartford
ORD
Chicago
$328 Roundtrip, found 1 day ago
$328
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Thu, Nov 5 from Hartford to Chicago, returning Mon, Nov 9, priced at $328 found 1 day 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 26 to May 27
$148 total
May 26 - May 27
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! (2,662 reviews)
Staff was wonderful.

Reviewed on May 3, 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
$144 nightly
The price is $171 total per night from May 26 to May 27
$171 total
May 26 - May 27
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! (5,156 reviews)
Staff was very friendly!

Reviewed on May 3, 2026

Opens in a new windowRiver Hotel
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 $253 total per night from May 23 to May 24
$253 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! (2,273 reviews)
Good for an airport hotel. Definitely dated.

Reviewed on May 2, 2026

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

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$151 nightly
The price is $180 total per night from May 27 to May 28
$180 total
May 27 - May 28
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! (4,034 reviews)
OK stay Could be better Wouldn’t stay again

Reviewed on May 3, 2026

Opens in a new windowHotel Riu Plaza Chicago
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 10 to May 11
$138 total
May 10 - May 11
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! (3,478 reviews)
Staff was wonderful. Great location for exploring the city!

Reviewed on May 3, 2026

Opens in a new windowClub Quarters Hotel, Central Loop, 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! (4,247 reviews)
I don’t understand the excellent reviews at this hotel. The hotel was in a great location. However the room was very dated and smelled of mildew and mold. Shower was filthy. Furniture was falling apart. Would not stay here again.

Reviewed on May 2, 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! (2,291 reviews)
clean room, wonderful pool, breakfast was very good, everything felt effortless.

Reviewed on Apr 30, 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
$125 nightly
The price is $149 total per night from May 8 to May 9
$149 total
May 8 - May 9
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! (10,134 reviews)
The room was ok, no thermostat to control temp and was warmer than i would have liked. The bed was hard and made my back hurt. Staff did not answer the phone for about 30 min between 4 calls that i made before getting extra pillows. The doorman called transport for us and it took forever for him ...

Reviewed on May 3, 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.